Shaping 1,2,4-Triazolium Fluorinated Ionic Liquid Crystals

2023

The synthesis and thermotropic behaviour of some di-alkyloxy-phenyl-1,2,4-triazolium trifluoromethane-sulfonate salts bearing a seven-carbon atom perfluoroalkyl chain on the cation is herein described. The fluorinated salts presenting a 1,2,4-triazole as a core and differing in the length of two alkyloxy chains on the phenyl ring demonstrated a typical liquid crystalline behaviour. The mesomorphic properties of this set of salts were studied by differential scanning calorimetry and polarized optical microscopy. The thermotropic properties are discussed on the grounds of the tuneable structures of the salts. The results showed the existence of a monotropic, columnar, liquid crystalline phase…

Chemistry of Fluorinated Oxadiazoles and Thiadiazoles

2014

A literature survey of the chemistry of fluorinated oxadiazoles and thiadiazoles is presented. The core part on synthetic procedures is given by type of heterocycle and includes recent developments up to the end of 2012. Reactivity is discussed when induced by the presence of the fluorinated moiety. Selected examples of bioactive compounds and applications are illustrated.

The new era of 1,2,4-oxadiazoles

2009

The synthesis, the chemical and photochemical reactivity, and the use of 1,2,4-oxadiazoles in materials and as bioactive compounds have been reviewed. The material in this survey includes some historical background, general features, state-of-the-art applications together with a critical discussion about current limitations and suggestions for future developments.

Fluorinated heterocyclic compounds. A photochemical synthesis of 3-amino-5-perfluoroaryl-1,2,4-oxadiazoles

2001

Abstract A photochemical methodology for the synthesis of 3-amino- (or 3- N -substituted amino) 5-pentafluorophenyl-1,2,4-oxadiazoles is reported. Irradiation of 3-pentafluorobenzoylamino-4-methyl-1,2,5-oxadiazole (Furazan) at 254 nm in methanol and in the presence of ammonia, primary or secondary aliphatic amines produces 3-amino-, 3-( N -alkylamino)-, 3-( N , N -dialkylamino)-5-pentafluorophenyl-1,2,4-oxadiazoles. The photoreaction follows the fragmentation pattern of the furazan ring with the extrusion of acetonitrile and the formation of a counterpart fragment which the nitrogen nucleophile will capture. Depending on the nature of the reagent, displacement of a fluoride anion at the C(5…

Low-density-lipoprotein peak particle size in a Mediterranean population

2003

Background The predominance of small, dense low-density lipoprotein (LDL) particles (‘LDL phenotype B’) has been associated with a three-fold increased risk of myocardial infarction, but the feasibility of the identification of small, dense LDL as independent predictors of coronary artery disease risk in population studies remains questioned. Design We evaluated the LDL peak particle size and its relation with other established risk factors for coronary heart disease in a group of 156 randomized subjects living on the Mediterranean island of Ustica (71 males and 85 women, range of age 20–69 years), representing approximately 30% of the total population. Results The prevalence of LDL phenoty…

Presence and biodistribution of perfluorooctanoic acid (PFOA) in Paracentrotus lividus highlight its potential application for environmental biomonit…

2021

AbstractThe first determination of presence and biodistribution of PFOA in ninety specimens of sea urchin Paracentrotus lividus from two differently contaminated sites along Palermo’s coastline (Sicily) is reported. Analyses were performed on the sea urchins’ coelomic fluids, coelomocytes, gonads or mixed organs, as well as on seawater and Posidonia oceanica leaves samples from the collection sites. PFOA concentration ranged between 1 and 13 ng/L in seawater and between 0 and 794 ng/g in P. oceanica. The analyses carried out on individuals of P. lividus from the least polluted site (A) showed PFOA median values equal to 0 in all the matrices (coelomic fluid, coelomocytes and gonads). Conver…

Fluorinated and pegylated polyaspartamide derivatives to increase solubility and efficacy of Flutamide

2012

New fluorinated amphiphilic copolymers based on a biocompatible polyaspartamide have been prepared in order to obtain polymeric micelles useful for delivering anticancer drugs. In particular, α,β-poly(N-2-hydroxyethyl)-d,l-aspartamide (PHEA) has been derivatized with polyethylene glycol (PEG(2000)) and ethylendiamine (EDA). Both these portions form the hydrophilic part of the copolymer, while the hydrophobic moiety is given by 1,2,4-oxadiazoles: 5-pentafluorophenyl-3-perfluoroheptyl-1,2,4-oxadiazole (PPOX) or 3-carboxyethyl-5-pentadecafluoroheptyl-1,2,4-oxadiazole (CPOX). Copolymers named PHEA-PEG(2000)-EDA-PPOX and PHEA-PEG(2000)-EDA-CPOX have been prepared with various degrees of derivati…

Premature termination codon 124 derivatives as a novel approach to improve the read-through of premature amber and ochre stop codons

2015

Nucleotide changes within an exon may alter the trinucleotide normally encoding a particular amino acid, such that a new stop signal is transcribed into the mRNA open reading frame. A recent approach to directly overcome the deleterious effects caused by nonsense mutations is represented by readthrough strategies which take advantage of the known properties of aminoglycosides that can suppress stop codons.

Nonsense codons suppression. An acute toxicity study of three optimized TRIDs in murine model, safety and tolerability evaluation.

2022

Stop mutations cause 11% of the genetic diseases, due to the introduction of a premature termination codon (PTC) in the mRNA, followed by the production of a truncated protein. A promising therapeutic approach is the suppression therapy by Translational Readthrough Inducing Drugs (TRIDs), restoring the expression of the protein. Recently, three new TRIDs (NV848, NV914, NV930) have been proposed, and validated by several in vitro assays, for the rescue of the CFTR protein, involved in Cystic Fibrosis disease. In this work, an acute toxicological study for the three TRIDs was conducted in vivo on mice, according to the OECD No.420 guidelines. Animals were divided into groups and treated with …

Rearrangements of 1,2,4-Oxadiazole: “One Ring to Rule Them All”

2017

[Figure not available: see fulltext.] 1,2,4-Oxadiazoles are heterocycles characterized by low aromaticity and the presence of a weak O–N bond and are widely studied due to their tendency to rearrange into more stable heterocyclic compounds. This review covers literature from the last fifteen years, highlighting the general features of 1,2,4-oxadiazoles and their applications. Regarding the reactivity, the development of classical reactions (thermal and photochemical rearrangements) is presented in terms of synthetic utility and mechanistic insight. Among the relevant rearrangement reactions, the Boulton–Katritzky Rearrangement (BKR), Migration – Nucleophilic Attack – Cyclization (MN…

COMBINING TRANSLATION READTHROUGH INDUCING DRUGS AND NONSENSE MEDIATED DECAY PATWHAY INHIBITION TO THE CFTR RESCUE IN CYSTIC FIBROSIS CELL MODEL SYST…

2021

Nonsense mutations affect 10% of patients with cystic fibrosis and produce a premature termination codon in CFTR (Cystic Fibrosis Transmembrane Conductance Regulator) mRNA causing early termination of translation and leading to lack of CFTR function. A potential therapy for nonsense mutations provides the use of small molecules able to overcome the premature stop codon (PTC) by a readthrough mechanism that lead to synthesis a complete CFTR protein. Despite the good results obtained from this approach, TRIDs efficiency is considerably reduced by the poor amount of target transcript, that is the mRNA containing the PTC. The readthrough, indeed, does not occur on the totality of target transcr…

RESCUE OF LRBA GENE EXPRESSION IN PRIMARY HUMAN FIBROBLASTS CHARACTERISED BY NONSENSE MUTATION c. 5047 (C>T).

2021

Primary immunodeficiencies (PIDs) are rare genetic diseases characterized by susceptibility to infections, increased risk of autoimmunity, hypogammaglobulinemia, and lymphoproliferative syndromes. PIDs are associated to genetic alterations in about 400 known genes, among which, mutations of the LRBA gene. LRBA gene encodes a widely expressed multi-domain protein with highly conserved BEACH domain, involved in regulation of endosomal trafficking, particularly endocytosis of ligand-activated receptors. It was reported that stop mutations affect this gene leading to the loss of the protein expression. Recently, we identified three Translational Readthrough Inducing Drug (TRID), that showed hig…

Fluorinated Heterocyclic Compounds. A Photochemical Approach to a Synthesis of Polyfluoroaryl-1,2,4-triazoles.

2005

The reaction of some fluorinated 1,2,4-oxadiazoles in the presence of methylamine or propylamine has been investigated. The irradiation in methanol or acetonitrile leads with acceptable yields to the corresponding fluorinated 1- methyl- or 1-propyl-1,2,4-triazole.

Identification and validation of novel molecules obtained by integrated computational and experimental approaches for the read-through of PTCs in CF …

2015

Synthesis of trifluoromethylated 2-benzoyl- and 2-aminoimidazoles from ring rearrangement of 1,2,4-oxadiazole derivatives

2008

Abstract Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5-phenyl-1,2,4-oxadiazole with fluorinated β-dicarbonyl compounds and subsequent base-induced Boulton–Katritzky Rearrangement (BKR) of the isolated β-enaminocarbonyl intermediate. Alternatively, one-pot reactions performed in the presence of Montmorillonite K10 favoured the condensation at the 3-amino moiety of the oxadiazole and, in some cases, allowed the direct synthesis of 2-benzoylamino-imidazoles. Hydrolysis of 2-benzoylamino-imidazoles easily yielded fluorinated 2-amino-imidazoles targets.

Competing Ring-Photoisomerization Pathways in the 1,2,4-Oxadiazole Series. An Unprecedented Ring-Degenerate Photoisomerization

2002

The irradiation of some 5-alkyl-3-amino-1,2,4-oxadiazoles at lambda = 254 nm in methanol in the presence of triethylamine (TEA) gave ring-photoisomerization both into 2-alkyl-5-amino-1,3,4-oxadiazoles and, unprecedently, into the ring-degenerate 3-alkyl-5-amino-1,2,4-oxadiazoles. The competing ring contraction-ring expansion route and the internal cyclization-isomerization mechanism explain the results.

ChemInform Abstract: Synthesis of 4(5)-Phenacyl-imidazoles from Isoxazole Side-Chain Rearrangements.

2011

The reaction must be carried out under nitrogen atmosphere in deoxygenated solvent to prevent the oxidation of the imidazole products.

Deciphering the Nonsense Readthrough Mechanism of Action of Ataluren: An in Silico Compared Study

2019

Ataluren was reported to suppress nonsense mutations by promoting the readthrough of premature stop codons, although its mechanism of action (MOA) is still debated. The likely interaction of Ataluren with CFTR-mRNA has been previously studied by molecular dynamics. In this work we extended the modeling of Ataluren's MOA by complementary computational approaches such as induced fit docking (IFD), quantum polarized ligand docking (QPLD), MM-GBSA free-energy calculations, and computational mutagenesis. In addition to CFTR-mRNA, this study considered other model targets implicated in the translation process, such as eukaryotic rRNA 18S, prokaryotic rRNA 16S, and eukaryotic Release Factor 1 (eRF…

Effect of protonation and deprotonation on the gas phase reactivity of fluorinated 1,2,4-triazines

2008

Positive and negative electrospray mass spectrometry (MS), in-time and in-space MS n experiments, high-resolution and accurate mass measurements obtained with an Orbitrap, together with density functional theory calculations have been used to study the gas-phase ion chemistry of a series of fluorinated 1,2,4-triazines. As a result of low-energy collision-induced dissociations, occurring in an ion trap and in a triple quadrupole, their protonated and deprotonated molecules show interesting features depending on the nature and structure of the precursor ions. The occurrence of elimination/hydration reactions produced by positive ions in the ion trap is noteworthy. Decompositions of deprotonat…

Chaperonotherapy for Alzheimer’s Disease: Focusing on HSP60

2015

This review will analyze growing evidence suggesting a convergence between two major areas of research: Alzheimer’s disease (AD) and chaperonopathies. While AD is a widely recognized medical, public health, and social problem, the chaperonopathies have not yet been acknowledged as a related burden of similar magnitude. However, recent evidence collectively indicates that such possibility exists in that AD, or at least some forms of it, may indeed be a chaperonopathy. The importance of considering this possibility cannot be overemphasized since it provides a novel point of view to examine AD and potentially suggests new therapeutic avenues. In this review, we focus on the mitochondrial chape…

Environmental Organic Photochemistry: Advances and Perspectives

2013

This review is a survey of recent advances in environment related aspects of organic photochemistry. Besides presenting gen- eral concepts, the manuscript is mainly focused on the photoreactivity of natural organic matter, and on the photochemistry of anthropo- genic substances under natural light irradiation.

Flavouring Extra-Virgin Olive Oil with Aromatic and Medicinal Plants Essential Oils Stabilizes Oleic Acid Composition during Photo-Oxidative Stress

2021

Essential oils (EOs) from medicinal and aromatic plants (MAPs) are well-known as natural antioxidants. Their addition to extra-virgin olive oil (EVOO) can contribute to reducing fat oxidation. The main aim of this study was to improve both food shelf-life and aromatic flavour of EVOO, adding different EOs of Sicilian accessions of common sage, oregano, rosemary and thyme. The morphological and production characteristics of 40 accessions of MAPs were preliminarily assessed. EOs from the most promising accessions of MAPs were analysed by gas-chromatography and mass spectrometry. Photo-oxidative studies of the EOs were carried out and the determination of the EVOO fatty acids obtained from 4 I…

Photochemical sample treatment for extracts clean up in PCB analysis from sediments.

2013

Sample purification can be considered the most polluting step of the whole analytical process for PCBs determination in sediment samples. The use of photochemical sample treatment represents an alternative methodology for extracts clean up allowing for a reduction of the used amount of organic solvents. The first application of a photochemical sample treatment for the selective removal or reduction of organic substances interfering with PCBs analyses in sediments is reported. The method's efficiency and robustness were compared with currently used chromatographic purification. Quality parameters such as recovery, linearity and reproducibility were studied. The entire procedure was validated…

Identification of a new molecule with readthrough activity to rescue CFTR protein function

In Cystic fibrosis (CF) disease nonsense mutations in the CFTR gene cause absence of the CFTR protein expression and a more severe form of the disease. About 10% of patient affected by CF show a nonsense mutation. A potential treatment of this alteration is to promote translational readthrough of premature termination codons (PTCs) by translational readthrough inducing drugs such as Ataluren. In this context we aimed to compare the 1,2,4-oxadiazole core of Ataluren with a slightly different scaffold, the 1,3,4oxadiazole core. By a validated protocol consisting of computational screening, synthesis and biological tests we identified, a new small molecule with 1,3,4-oxadiazole core (2a/NV2445…

Hsp60 Inhibitors and Modulators

2019

In this chapter, we focus on the 60 KDa Heat Shock Protein (Hsp60) and discuss some of its biological, molecular and pathological features. The structural and mechanistic aspect of the Hsp60 folding cycle will be also presented. We further illustrate how Hsp60 may be involved in many diseases and therefore considered as an effective therapeutic or theranostic target. Finally, the state-of-the-art on the development of Hsp60 and bacterial GroEL inhibitors and modulators of their expression will be illustrated. This is discussed in the light of a negative chaperonotherapy, and the consequent development of inhibitors, as well as positive chaperonotherapy, in the event its excessive activity i…

Fluoropolymer Based on a Polyaspartamide containing 1,2,4-Oxadiazole Units: A Potential Artificial Oxygen (O2) Carrier

2007

Abstract In this preliminary work we have prepared a fluorinated polymer capable of solubilizing an appreciable amount of O(2) and, at the same time, maintaining a higher water solubility than perfluoroalkanes investigated as injectable O(2) carriers. In particular, we describe the synthesis and characterization of a new macromolecular conjugate obtained by derivatization of alpha,beta-poly(N-2-hydroxyethyl)-DL-aspartamide (PHEA) with 5-pentafluorophenyl-3-perfluoroheptyl-1,2,4-oxadiazole, called PHEA-F. This new water soluble fluoropolymer was prepared in high yield using a simple procedure. It was characterized by FT-IR and UV-vis spectrophotometry, (19)F-NMR and SEC measurements. O(2) so…

Dissecting the packing forces in mixed perfluorocarbon/aromatic co-crystals

2021

We carried out a systematic evaluation of the packing forces in co-crystals featuring monoiodo- and diiodo-perfluoroalkanes and 1,2,4-oxadiazoles through single crystal X-ray diffraction and theoretical analysis. The molecules assemble via a combination of halogen bonding and specific dispersive interactions involving the perfluorinated units. We quantitatively elucidated the nature and strength of such interactions through solid-state calculations and Hirshfeld surface analysis. One of the co-crystals, formed by two monoiodoperfluorodecane molecules, the longest perfluorinated chain ever solved at the atomic level, allowed us to fully highlight the role of fluorous interactions.

Enhancement of premature stop codon readthrough in the CFTR gene by Ataluren (PTC124) derivatives.

2015

Abstract Premature stop codons are the result of nonsense mutations occurring within the coding sequence of a gene. These mutations lead to the synthesis of a truncated protein and are responsible for several genetic diseases. A potential pharmacological approach to treat these diseases is to promote the translational readthrough of premature stop codons by small molecules aiming to restore the full-length protein. The compound PTC124 (Ataluren) was reported to promote the readthrough of the premature UGA stop codon, although its activity was questioned. The potential interaction of PTC124 with mutated mRNA was recently suggested by molecular dynamics (MD) studies highlighting the importanc…

Synthesis of fluorinated first generation starburst molecules containing a triethanolamine core and 1,2,4-oxadiazoles

2006

Abstract 5-Pentafluorophenyl-1,2,4-oxadiazoles, differently substituted at C(3), have been synthesized and used to functionalize the aliphatic primary hydroxyl functionalities of triethanolamine, under mild conditions. UV–visible absorption and emission spectra are reported, for both tri- and difunctionalised molecules, showing their potential applications as light-emitters in optoelectronic devices.

Characterization of isomeric 1,2,4-oxadiazolyl-N-methylpyridinium salts by electrospray ionization tandem mass spectrometry.

2007

The mass spectrometric behavior of 1,2,4-oxadiazolyl- N-methylpyridinium salts has been investigated. These substances are of current interest as perspective ionic liquids, compounds used as green solvents for synthesis, and for their catalytic properties. The studies have been developed through electrospray ionization tandem mass spectrometry (ESI-MS/MS) experiments. The obtained results demonstrate a ready distinction between the two isomeric classes, 3- N-methylpyridinium- and 5- N-methylpyridinium-1,2,4-oxadiazoles, is possible through ESI-MS/MS experiments. A deeper investigation on the principal fragmentation pathways of characteristic ions has been also developed.

Solvent dependent photochemical reactivity of 3-allyloxy-1,2,4-oxadiazoles

2009

Photoluminescent decoration of iron oxide magnetic nanoparticles for dual-imaging applications

2018

A selective functionalization of dopamine amino group with the photoluminescent 7-nitroben-zofurazan was achieved through a one-pot protection-functionalization-deprotection sequence. The resulting fluorescent catecholic ligand was used as a capping agent for iron oxide nanoparticles thus obtaining photoluminescent magnetic nanoparticles (PL-MNPs). The PL-MNPs were then embedded into PLGA-b-PEG polymeric nanocarriers which quenched the emission of the capping agent. Full recovery of fluorescence was observed after disassembling the polymeric layer of the nanoparticle, thus supporting the use of PL-MNPs as a multifunctional system for targeted drug delivery.

NOVEL SMALL MOLECULES THAT BIND AND/OR MODULATE DIFFERENT FORMS OF TAU OLIGOMERS

2020

The present invention relates to novel small molecules of Formulas I, II, III, IIIa, IIIb, and IV and pharmaceutically acceptable salts thereof, as well as the preparation and the use thereof.

A Generalized Synthesis of 3-Amino-5-aryl-, 3-Amino-5-polyfluorophenyl-, and 3-Amino-5-alkyl-1,2,4-oxadiazoles through Ring-degenerate Rearrangements

2002

A generalized synthesis of 3-amino-5-aryl-, 3-amino-5-poly- fluorophenyl- and 3-amino-5-alkyl-1,2,4-oxadiazoles has been developed starting from the 3-amino-5-methyl-1,2,4-oxadiazole as a common synthon. Aroylation or alkanoylation of this aminooxadiazole, followed by thermally- induced ring-degenerate equilibration of resulting 3-acylamino compounds, and final acid hydrolysis of the 3-acetylamino-5-aryl- (or 5-polyfluorophenyl-), or 3- acetylamino-5-alkyl-1,2,4-oxadiazoles counterpart which is formed, gave the expected 3-amino-5-substituted 1,2,4-oxadiazoles. In the case of some 3- aroylamino compounds, yields of final 3-amino-5-aryloxadiazoles are higher than that expected on the basis of…

Novel Translational Read-through–Inducing Drugs as a Therapeutic Option for Shwachman-Diamond Syndrome

2022

Shwachman-Diamond syndrome (SDS) is one of the most commonly inherited bone marrow failure syndromes (IBMFS). In SDS, bone marrow is hypocellular, with marked neutropenia. Moreover, SDS patients have a high risk of developing myelodysplastic syndrome (MDS), which in turn increases the risk of acute myeloid leukemia (AML) from an early age. Most SDS patients are heterozygous for the c.183-184TA>CT (K62X) SBDS nonsense mutation. Fortunately, a plethora of translational read-through inducing drugs (TRIDs) have been developed and tested for several rare inherited diseases due to nonsense mutations so far. The authors previously demonstrated that ataluren (PTC124) can restore full-length SBDS…

Uptake and photoinduced degradation of phthalic acid esters (PAEs) in Ulva lactuca highlight its potential application in environmental bioremediation

2022

Abstract The bioaccumulation of phthalates was studied in fragments of Ulva lactuca exposed for a maximum of 31 days at different concentrations of a solution of six phthalic acid esters (PAEs). The algal matrix showed rapid uptake since the first sampling, which increased over the time of the experimental period, at the end of which seaweed’s bioaccumulation potential was also evaluated. After the uptake, the algal matrix was subjected to UV irradiation in order to verify the removal of the phthalates. PAEs with higher octanol–water partition coefficients (logKow) and molecular weights were preferentially uptaken by U. lactuca in all the exposure experiments. It was observed that both accu…

Positive effect of the fluorine moiety on the oxygen storage capacity of UiO-66 metal–organic frameworks

2016

Two series of fluorine-containing UiO-66 have been synthesized, replacing the 1,4-benzodicarboxylic acid linker with increasing amounts of 2-fluoro-1,4-benzodicarboxylic acid or 2-trifluoromethyl-1,4-benzodicarboxylic acid. The capacity to store oxygen and nitrogen within these MOFs has been tested, which revealed a positive correlation between the fluorine content and the oxygen storage performances.

The dissociation of the Hsp60/pro-Caspase-3 complex by bis(pyridyl)oxadiazole copper complex (CubipyOXA) leads to cell death in NCI-H292 cancer cells

2017

Abstract Cell survival and proliferation are central to carcinogenesis, involving various mechanisms among which those that impede apoptosis are important. In this, the role of the molecular chaperone Hsp60 is unclear since it has been reported that it can be both, pro- or anti-apoptotic. A solution to this riddle is crucial to the development of anti-cancer therapies targeting Hsp60. We addressed this question using a tumor cell line, NCI-H292, and [Cu(3,5-bis(2′-pyridyl)-1,2,4-oxadiazole) 2 (H 2 O) 2 ](ClO 4 ) 2 , CubipyOXA , a copper-containing compound with cytotoxic properties. We treated cells with various doses of the compound and measured cell viability; apoptosis indicators; and le…

A new experimental protocol for intrazeolite photooxidations. The first product-based estimate of an upper limit for the intrazeolite singlet oxygen …

2002

The intrazeolite photooxidations of several alkenes have been examined in hexane and in perfluorohexane slurries. The ability of perfluorohexane to increase the affinity of alkenes for the interior of the zeolite was documented. The nearly identical reaction rates in the two slurry solvents are attributed to a leveling of the singlet oxygen lifetime by the zeolite framework. A consideration of the rates of the various intrazeolite processes was used to estimate an upper limit for the intrazeolite lifetime of singlet oxygen.

Fluorinated Heterocyclic Compounds. An Effective Strategy for the Synthesis of Fluorinated Z-Oximes of 3-Perfluoroalkyl-6-phenyl-2H-1,2,4-triazin- 5-…

2005

The reaction of 3-benzoyl-5-perfluoroalkyl-1,2,4-oxadiazoles with hydrazine has been investigated, evidencing the possibility of competitive reaction paths. Nucleophilic addition of the hydrazine to the electrophilic C(5) of the 1,2,4-oxadiazole ring, followed by ring opening and ring closure with enlargement, leads with high yield and in very mild experimental conditions to the formation of Z-oximes of 3-perfluoroalkyl-6-phenyl-2H-1,2,4-triazin-5-ones (11a-c) as major products of the reaction. In turn, the hydrazine can attack the electrophilic carbonyl carbon giving 4-perfluoroacylamino-5-phenyl-2H-1,2,3-triazoles (13a-c) through the well-known Boulton-Katritzky rearrangement of the inter…

Impact of Heavy Metals in Eggs and Tissues of C. caretta along the Sicilian Coast (Mediterranean Sea)

2022

In this study we compared the heavy metal concentration found in different tissues and eggs of the loggerhead sea turtle and evaluated the potential ecotoxicological risk for this important species. Eighteen heavy metal elements were determined in different tissues (liver, gonads, fat, kidney, heart, brain, and spleen) of nine individuals of Caretta caretta found stranded along the coasts of Messina (Sicily, Italy) and in the shell and yolk of six eggs from the island of Linosa (Sicily, Italy). For the analysis of the heavy metals, we used the analytical procedures in accordance with the EPA 200.8 method supplemented by EPA 6020b with three replicates for each measurement. The elements anal…

New linezolid-like 1,2,4-oxadiazoles active against Gram-positive multiresistant pathogens

2013

The synthesis and the in vitro antibacterial activity of novel linezolid-like oxadiazoles are reported. Replacement of the linezolid morpholine C-ring with 1,2,4-oxadiazole results in an antibacterial activity against Staphylococcus aureus both methicillin-susceptible and methicillin-resistant comparable or even superior to that of linezolid. While acetamidomethyl or thioacetoamidomethyl moieties in the C(5) side-chain are required, fluorination of the phenyl B ring exhibits a slight effect on an antibacterial activity but its presence seems to reduce the compounds cytotoxicity. Molecular modeling performed using two different approaches - FLAP and Amber software - shows that in the binding…

Investigating the inhibition of FTSJ1 a tryptophan tRNA-specific 2’-O-methyltransferase by NV TRIDs, as a mechanism of readthrough in nonsense mutate…

2023

Abstract: Cystic Fibrosis (CF) is an autosomal recessive genetic disease caused by mutations in the CFTR gene, coding for the CFTR chloride channel. About 10% of the CFTR gene mutations are "stop" mutations, which generate a Premature Termination Codon (PTC), thus synthesizing a truncated CFTR protein. A way to bypass PTC relies on ribosome readthrough, which is the ri-bosome’s capacity to skip a PTC, thus generating a full-length protein. “TRIDs” are molecules exerting ribosome readthrough; for some, the mechanism of action is still under debate. We in-vestigate a possible mechanism of action (MOA) by which our recently synthesized TRIDs, namely NV848, NV914, and NV930, could exert their r…

Synthesis of Tetrasubstituted 4,4'-Biimidazoles

2012

Highly substituted 4,4'-biimidazoles were synthesized, in good to excellent yields, through a multicomponent imidazole ring synthesis by using imidazol-4-yl-ethane-1,2-diones as starting materials. The obtained compounds were preliminarily tested as chromogenic and fluorescent sensors for heavy metals.

Heterocyclic Scaffolds for the Treatment of Alzheimer's Disease

2016

Background: The treatment and diagnosis of Alzheimer’s Disease (AD) are two of the most urgent goals for research around the world. The cognitive decline is generally associated with the elevated levels of extracellular senile plaques, intracellular neurofibril- lary tangles (NFTs), and with a progressive shutdown of the cholinergic basal forebrain neurons transmission. Even if several key targets are under fervent investigation in the cure of AD, till now, the only approved therapeutic strategy is the treatment of symptoms by using cholinesterases inhibitors. It has been demonstrated that both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes are not only responsible of…

Photochemical Functionalization of Allyl Benzoates by C-H Insertion

2013

The photoreactivity of allyl benzoates, containing an electron-rich double bond, has been explored by irradiation at 305 nm in different solvents. Solvent addition products arising from an insertion of the alpha H–C bonds of THF, dioxane, and i-PrOH to the allylic double bond was realized. The observed reactivity depended on reaction conditions and substitution pattern of the substrate. A DFT study on this unusual reaction was performed allowing the formulation of two mechanistic pathways.

Synthesis and chemical characterization of CuII, NiII and ZnII complexes of 3,5-bis(2′-pyridyl)-1,2,4-oxadiazole and 3-(2′-pyridyl)5-(phenyl)-1,2,4-o…

2011

Abstract The synthesis and structural characterization of Ni II , Cu II and Zn II complexes of two chelating 1,2,4-oxadiazole ligands, namely 3,5-bis(2′-pyridyl)-1,2,4-oxadiazole (bipyOXA) and 3-(2′-pyridyl)5-(phenyl)-1,2,4-oxadiazole (pyOXA), is here reported. The formed hexacoordinated metal complexes are [M(bipyOXA) 2 (H 2 O) 2 ](ClO 4 ) 2 and [M(pyOXA) 2 (ClO 4 ) 2 ], respectively (M = Ni, Cu, Zn). X-ray crystallography, 1 H and 13 C NMR spectroscopy and C, N, H elemental analysis data concord in attributing them an octahedral coordination geometry. The two coordinated pyOXA ligands assume a trans coplanar disposition, while the two bipyOXA ligands are not. The latter result is a possib…

Photochemical sample treatment: a greener approach to chlorobenzene determination in sediments.

2014

Abstract Due to worker׳s exposure, solvent and stationary phases׳ consumption, sample purification is one of the most polluting steps in analytical procedures for determination of organic pollutants in real samples. The use of photochemical sample treatment represents a valid alternative methodology for extracts clean up allowing for a reduction of the used amount of organic solvents. In this paper we report the first application on the photolytic destruction of organic substances to eliminate some of the interferences in the analysis of Chlorobenzenes in sediment samples. The method׳s efficiency and robustness were compared with classic silica column purification process currently used in …

Synthesis, characterization, cellular uptake and interaction with native DNA of a bis(pyridyl)-1,2,4-oxadiazole copper(II) complex

2010

The copper(II) complex of 3,5-bis(2'-pyridyl)-1,2,4-oxadiazole was synthesized and characterized. X-Ray crystallography revealed that the complex consists of a discrete [Cu(3,5-bis(2'-pyridyl)-1,2,4-oxadiazole)(2)(H(2)O)(2)](2+) cation and two ClO(4)(-) anions. The Cu(II) coordination sphere has a distorted octahedral geometry and each ligand chelates the copper ion through the N(4) nitrogen of the oxadiazole ring and the nitrogen of one pyridine moiety. The coordinated water molecules are in cis position and each of them is H-bonded to the 5-pyridyl nitrogen of the oxadiazole ligand and to an oxygen of the perchlorate anion. Biological assays showed that, despite the free ligand not being …

Halogen bond directionality translates tecton geometry into self-assembled architecture geometry

2013

The structures of halogen-bonded infinite chains involving two diiodoperfluoroalkanes and a bent bis(pyrid-4′-yl)oxadiazole show that the geometry of the pyridyl pendant rings is translated into the angle between the formed halogen bonds.

Oxadiazolyl-Pyridinium as Cationic Scaffold for Fluorinated Ionic Liquid Crystals

2021

The synthesis and characterization of a new class of 1,2,4-oxadiazolylpyridinium as a cationic scaffold for fluorinated ionic liquid crystals is herein described. A series of 12 fluorinated heterocyclic salts based on a 1,2,4-oxadiazole moiety, connected through its C(5) or C(3) to an N-alkylpyridinium unit and a perfluoroheptyl chain, differing in the length of the alkyl chain and counterions, has been synthesized. As counterions iodide, bromide and bis(trifluoromethane)sulfonimide have been considered. The synthesis, structure, and liquid crystalline properties of these compounds are discussed on the basis of the tuned structural variables. The thermotropic properties of this series of sa…

Heterocyclic rearrangements in constrained media. A zeolite-directed photorearrangement of 1,2,4-oxadiazoles

2005

[reaction: see text] The first intrazeolite-photoinduced rearrangement of a five-membered heterocycle is reported. A completely different behavior compared to solution irradiations has been observed. The zeolite's role in directing the photoreaction of 3-phenyl-1,2,4-oxadiazoles toward the formation of the corresponding 1,3,4-oxadiazoles in a ring contraction-ringexpansion route is discussed.

An ANRORC approach to the synthesis of perfluoroalkylated 1,2,4-triazole-carboxamides

2009

A series of perfluoroalkyl-1,2,4-triazole-carboxamides has been obtained through an ANRORClike rearrangement (Addition of Nucleophile, Ring-Opening and Ring-Closure) of 5- perfluoroalkyl-1,2,4-oxadiazole-3-carboxamides with methylhydrazine or hydrazine. The initial addition of the bidentate nucleophile to the electrophilic C(5) of the 1,2,4-oxadiazole ring, followed by ring opening and ring closure, leads to the formation of triazoles in good yield under mild experimental conditions. In some cases, a competitive ANRORC-enlargement reaction to form 1,2,4-triazin-6-ones was also observed. Obtained carboxamidotriazoles have also been explored as precursors for the synthesis of 3(5)-perfluoroal…

ChemInform Abstract: Synthesis of Tetrasubstituted 4,4′-Biimidazoles.

2012

Highly substituted 4,4′-biimidazoles were synthesized, in good to excellent yields, through a multicomponent imidazole ring synthesis by using imidazol-4-yl-ethane-1,2-diones as starting materials. The obtained compounds were preliminarily tested as chromogenic and fluorescent sensors for heavy metals.

The innovative role of the readthrough inducing drugs in the translation rescue of mRNAs characterized by premature stop codon (PTCs).

On the structure of 3-acetylamino-5-methyl-1,2,4-oxadiazole and on the fully degenerate rearrangements (FDR) of its anion: a stimulating comparison b…

2009

An accurate crystal structure determination has provided evidence for a planar conformation for 3-acetylamino-5-methyl-1,2,4-oxadiazole (5), in agreement with quantum-mechanical calculations in the gas phase. In the crystal, a series of strong intermolecular N7H7….O9 hydrogen bonds link the amido groups of different molecules, causing the formation of infinite parallel ordered chains. The effect of the DMSO solvent on the energy and charge distribution of compound 5 and on its relevant 5− anion, involved in a fully degenerate rearrangement (FDR), has been deepened by quantum-mechanical DFT calculations. The calculated energy barrier for the FDR increases in going from in vacuo to DMSO, in a…

On the reaction of some 5-polyfluoroaryl-1,2,4-oxadiazoles with methylhydrazine: synthesis of fluorinated indazoles

2009

The reaction of 5-polyfluoroaryl-1,2,4-oxadiazoles with methylhydrazine has been studied and the synthesis of fluorinated N-methylindazoles has been realized. Rearrangement reactions showed predominantly formation of N(1)-methylindazole regioisomers. Starting compounds were preliminarily functionalized at the polyfluoroaryl moiety through fluorine displacement with nucleophiles (methanol, methylamine, dimethylamine), allowing the obtainment of target indazoles substituted at the C(6) position.

Fluorinated Heterocyclic Compounds− The First Example of an Irreversible Ring-Degenerate Rearrangement on Five-Membered Heterocycles by Attack of an …

2004

The reactions of 5-perfluoroalkyl-1,2,4-oxadiazoles 3 with hydroxylamine in DMF give the regioisomeric 3-perfluoroalkyl-1,2,4-oxadiazoles 4 in excellent yields. This process is the first example of ring-degenerate rearrangement (RDR) occurring on five-membered heterocycles by attack of an external bidentate nucleophile, which replaces two heteroatoms of the ring. We suggest that an ANRORC-like mechanism occurs in which the addition of the nucleophilic nitrogen atom (NH2OH) on the C(5) atom of 3 is followed by ring opening and irreversible ring-degenerate closure by attack of the nucleophilic oxygen atom (=NOH) on the C(3) atom of the original ring, realizing an elegant and efficient synthes…

Rescuing CFTR Protein Function: 1,3,4-oxadiazoles versus 1,2,4-oxadiazoles as readthrough inducing drugs

In Cystic fibrosis (CF) disease nonsense mutations in the CFTR gene cause the absence of the CFTR protein expression and a more severe form of the disease. About 10% of patient affected by CF show a nonsense mutation. A potential treatment of this alteration is to promote translational readthrough of premature termination codons (PTCs) by translational readthrough inducing drugs such as Ataluren (1). We reported a rationale for Ataluren promoted readthrough of PTCs by computational approach and GFP-reporter cell-based assay (2) and the observed enhancement of readthrough activity by some Ataluren derivatives (3, 4). In this context we aimed to compare the 1,2,4-oxadiazole core of Ataluren w…

ChemInform Abstract: Fluoro Heterocycles. A Photochemical Methodology for the Synthesis of 3-Amino- and 3-(N-Alkylamino)-5-perfluoroalkyl-1,2,4-oxadi…

2000

Abstract A photochemical methodology for the synthesis of perfluoroalkyl-1,2,4-oxadiazoles has been described. 3-Amino- and 3-( N -alkylamino)-5-perfluoroalkyl-1,2,4-oxadiazoles have been prepared by irradiation of 3-perfluoroalkanoylamino-4-phenyl-1,2,5-oxadiazoles (furazans) at λ =313 nm in methanol and in the presence of ammonia or primary aliphatic amines.

Fluorinated heterocyclic compounds: an assay on the photochemistry of some fluorinated 1-oxa-2-azoles: an expedient route to fluorinated heterocycles

2004

Abstract Photoinduced heterocyclic rearrangements of ON bond-containing azoles have been claimed in the synthesis of target fluorinated heterocyclic compounds. In this context, the photochemical behavior of some fluorinated 1,2,4-oxadiazoles has been investigated. Irradiations of 3-amino-5-perfluoroalkyl-1,2,4-oxadiazoles at λ =313 nm in methanol gave open-chain products arising from a reaction of the nucleophilic solvent with either the first formed ring-photolytic species or with a nitrilimine moiety generated from it. Differently, irradiations in methanol with the presence of triethylamine (TEA) followed competing phototransposition pathways leading to the ring-isomers 2-amino-5-perfluo…

Synthesis of fluorinated 1,2,4-oxadiazin-6-ones through ANRORC rearrangement of 1,2,4-oxadiazoles

2009

Abstract The reaction of 3-ethoxycarbonyl-5-perfluoroalkyl-1,2,4-oxadiazoles with hydroxylamines has been investigated, evidencing the possibility of competitive reaction paths. Nucleophilic addition of hydroxylamine to the electrophilic C(5) of the 1,2,4-oxadiazole ring, followed by ring-opening and ring-closure with enlargement, leads to high yield and in very mild experimental conditions to the formation of 5-hydroxyamino-3-perfluoroalkyl-6 H -1,2,4-oxadiazin-6-ones, one of these presenting water gelation ability. In turn, reactions with N -methylhydroxylamine lead the exclusive formation of 4-perfluoroacylamino-2-methyl-2 H -1,2,5-oxadiazol-3-ones through the well known Boulton–Katritzk…

Synthesis of fluorinated oxadiazoles with gelation and oxygen storage ability

2012

A new family of fluorinated low molecular weight (LMW) gelators has been synthesized through SNAr substitution of 5-polyfluoroaryl-3-perfluoroheptyl-1,2,4-oxadiazoles with glycine ester. The obtained compounds give thermal and pH-sensitive hydrogels or thermo-reversible organogels in DMSO. Oxygen solubility studies showed the ability to maintain high oxygen levels in solution and in gel blend with plate counter agar (PCA).

ChemInform Abstract: Photochemical Functionalization of Allyl Benzoates by C-H Insertion.

2013

The photoreactivity of allyl benzoates, containing an electron-rich double bond, has been explored by irradiation at 305 nm in different solvents. Solvent addition products arising from an insertion of the alpha H–C bonds of THF, dioxane, and i-PrOH to the allylic double bond was realized. The observed reactivity depended on reaction conditions and substitution pattern of the substrate. A DFT study on this unusual reaction was performed allowing the formulation of two mechanistic pathways.

Hsp60 chaperonopathies and chaperonotherapy: targets and agents

2014

Hsp60 (Cpn60) assembles into a tetradecamer that interacts with the co-chaperonin Hsp10 (Cpn10) to assist client polypeptides to fold, but it also has other roles, including participation in pathogenic mechanisms.Hsp60 chaperonopathies are pathological conditions, inherited or acquired, in which the chaperone plays a determinant etiologic-pathogenic role. These diseases justify selection of Hsp60 as a target for developing agents that interfere with its pathogenic effects. We provide information on how to proceed.The information available encourages the development of ways to improve Hsp60 activity (positive chaperonotherapy) when deficient or to block it (negative chaperonotherapy) when pa…

Translational readthrough inducing drugs: a study of toxicity in mice models and in vitro safety validation of the specific readthrough process.

2022

Objective Nonsense mutations are responsible for 15% of Cystic Fibrosis (CF) patients due to the introduction of a premature stop codon (PTC) in the mRNA and the production of a truncated CFTR (Cystic Fibrosis Transmembrane Conductance Regulator) protein1. A promising therapeutic approach for stop mutations is the suppression therapy by Translational Readthrough Inducing Drugs (TRIDs) to restore the expression of the protein2,3. Recently three new TRIDS (NV848, NV914, NV930) have been proposed and validated by several assays. Our work was focused on TRIDs NV848, NV914, NV930. Important aspects of TRIDs to be evaluated are their specificity towards PTC, to demonstrate that TRIDs do not inter…

Synthesis of Isoxazoline Derivatives through Boulton-Katritzky Rearrangement of 1,2,4-Oxadiazoles

2013

The base-induced rearrangement of 1,2,4-oxadiazoles into isoxazoline derivatives is reported. This represents the first example of a three-atom side-chain rearrangement that involves a saturated CCO side chain at C-3 of the oxadiazole. Nonaromatic 3-amino-isoxazoline derivatives are obtained in good yields. Interestingly, this reaction occurs through the rearrangement of aromatic oxadiazoles to form less stable bonds than those that are broken.

FDA-Approved Fluorinated Heterocyclic Drugs from 2016 to 2022

2023

The inclusion of fluorine atoms or heterocyclic moiety into drug structures represents a recurrent motif in medicinal chemistry. The combination of these two features is constantly appearing in new molecular entities with various biological activities. This is demonstrated by the increasing number of newly synthesized fluorinated heterocyclic compounds among the Food and Drug Administration FDA-approved drugs. In this review, the biological activity, as well as the synthetic aspects, of 33 recently FDA-approved fluorinated heterocyclic drugs from 2016 to 2022 are highlighted.

Photoinduced molecular rearrangements. Some comments on the ring-photoisomerization of 1,2,4-oxadiazoles into 1,3,4-oxadiazoles

2001

The ring-photoisomerization of 3-amino- and 3-methylamino-5-phenyl-1,2,4-oxadiazoles into the corresponding 2-amino- and 2-methylamino-5-phenyl-1,3,4-oxadiazoles has been reinvestigated by examining the effect of a base on the photoreaction. On irradiating at λ = 254 nm in methanol, yields of the ring-photoisomers were found to be significantly enhanced by the addition of triethylamine (TEA) in the photoreaction medium. By contrast, irradiation of the 3-amino-5-phenyloxadiazole in acetonitrile containing TEA gave an almost complete photoreduction into benzoylguanidine, while few percent of the ring photoisomer were detected. Furthermore, the pyrene-sensitized photolysis of 3-amino-5-phenylo…

Autosomal recessive hypercholesterolemia in a Sicilian kindred harboring the 432insA mutation of the ARH gene

2003

Abstract We describe a Sicilian family presenting a recessive form of hypercholesterolemia harboring a mutation of the autosomal recessive hypercholesterolemia (ARH) gene. In two of the three sibs, a 26-year-old male and a 22-year-old female, a severe hypercholesterolemia was diagnosed with very high levels of plasma cholesterol (15.9 and 12.2 mmol/l, respectively); tendon xanthomatas and xanthelasms were present and in the male proband was documented a diffuse coronary atherosclerotic disease with a rapid and fatal progression. Both the parents had normal or slightly increased levels of plasma cholesterol. All causes of secondary hypercholesterolemia were ruled out as well as an involvemen…

Advances in singlet oxygen chemistry

2005

The authors discuss the advances made in both mechanistic and synthetic aspects of singlet oxygen chem.  Formation and reactions of singlet oxygen in heterogeneous media (such as zeolites, micelles, vesicles, etc.) are discussed.  Cycloaddns. of mol. oxygen to olefins, heteroatom oxidns. via reaction of singlet oxygen with the electron pair at heteroatoms, and photooxygenations of heterocyclic systems by singlet oxygen are also reviewed.

Lack of Dystrophin Affects Bronchial Epithelium inmdxMice

2016

Mild exercise training may positively affect the course of Duchenne Muscular Dystrophy (DMD). Training causes mild bronchial epithelial injury in both humans and mice, but no study assessed the effects of exercise in mdx mice, a well known model of DMD. The airway epithelium was examined in mdx (C57BL/10ScSn-Dmdmdx) mice, and in wild type (WT, C57BL/10ScSc) mice either under sedentary conditions (mdx-SD, WT-SD) or during mild exercise training (mdx-EX, WT-EX). At baseline, and after 30 and 45 days of training (5 d/wk for 6 weeks), epithelial morphology and markers of regeneration, apoptosis, and cellular stress were assessed. The number of goblet cells in bronchial epithelium was much lower…

Ammonium formate-Pd/C as a new reducing system for 1,2,4-oxadiazoles. Synthesis of guanidine derivatives and reductive rearrangement to quinazolin-4-…

2021

1,2,4-Oxadiazole is a heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NH4CO2H-Pd/C is here demonstrated as a new system for the O-N reduction, allowing us to obtain differently substituted acylamidine, acylguanidine and diacylguanidine derivatives. The proposed system is also effective for the achievement of a reductive rearrangement of 5-(2′-aminophenyl)-1,2,4-oxadiazoles into 1-alkylquinazolin-4(1H)-ones. The alkaloid glycosine was also obtained with this method. The obtained compounds were preliminarily tested for their biological activity in terms of their cytotoxicity, induce…

Hsp60, a Novel Target for Antitumor Therapy: Structure-Function Features and Prospective Drugs Design

2013

Heat shock protein 60 kDa (Hsp60) is a chaperone classically believed to be involved in assisting the correct folding of other mitochondrial proteins. Hsp60 also plays a role in cytoprotection against cell stressors, displaying for example, antiapoptotic potential. Despite the plethora of studies devoted to the mechanism of Hsp60's function, especially in prokaryotes, fundamental issues still remain unexplored, including the definition of its role in cancer. Key questions still unanswered pertain to the differences in structure-function features that might exist between the well-studied prokaryotic GroEL and the largely unexplored eukaryotic Hsp60 proteins. In this article we discuss these …

Derivati Ossadiazolici per il trattamento della fibrosi cistica: Readthrough di mutazioni nonsense

One-pot synthesis of fluorinated 2-amino-pyrimidine-N-oxides. Competing pathways in the four-atom side-chain rearrangements of 1,2,4-oxadiazoles

2006

Abstract Trifluoromethylated 2-amino-pyrimidine N-oxides have been synthesized by reaction of the 3-amino-5-methyl-1,2,4-oxadiazole with trifluoromethyl-β-diketones in the presence of perchloric acid, followed by hydrolysis. In this ring-to-ring transformation an initial formation of (unisolated) 1,2,4-oxadiazole-pyrimidinium salts, and subsequent ring-opening at the oxadiazole moiety occurs. Isolation of 2-(hydroxyamino)-pyrimidine from the reaction mixture evidenced the presence of a competing pathway where the N(4) nitrogen of the oxadiazole is involved in the formation of a regioisomeric pyrimidinium salt. The effect of the trifluoromethyl group on the product distribution is discussed.…

Fluorescent Hg2+ Sensors: Synthesis and Evaluation of a Tren-Based Starburst Molecule Containing Fluorinated 1,2,4-Oxadiazoles.

2010

A new tren-based starburst molecule containing fluorinated 1,2,4-oxadiazoles as fluorophores has been synthesized and its sensing behavior toward several metal cations has been investigated by UV/Vis, fluorescence, 1 H NMR and 19 F NMR spectroscopy. Selective sensing for Hg 2+ ions through a PET-based mechanism was evidenced, suggesting application as fluorescent sensor for Hg 2+ of the off-on type.

Ionic self assembly in the design of fluorinated ionic liquid crystals (ILCs)

2011

Ionic liquid crystals are a class of compounds containing anions and cations, that combine the properties of liquid crystals and ionic liquids[1]. In the conventional design of ionic liquid crystalline compounds, an ionic core is connected with mesogenic groups via chemical covalent bonding . Alternatively, in ionic compounds, strong electrostatic interactions between cation and anion can be used to build up liquid crystalline order at supramolecular level. This general approach, called ionic self-assembly (ISA), allows one to create ionic phases and mesophases with highly organized supramolecular order [2]. In this context, a new series of fluorinated ionic liquids (ILs) and ionic liquid c…

ChemInform Abstract: Synthesis of Isoxazoline Derivatives Through Boulton-Katritzky Rearrangement of 1,2,4-Oxadiazoles.

2013

This is the first report of the rearrangement of 1,2,4-oxadiazole with saturated C—C—O side chains and an unusual example of an irreversible rearrangement that allows the formation of nonaromatic heterocycles.

ChemInform Abstract: Fluorinated Heterocyclic Compounds. A Photochemical Synthesis of 3-Amino-5-perfluoroaryl-1,2,4-oxadiazoles.

2010

Abstract A photochemical methodology for the synthesis of 3-amino- (or 3- N -substituted amino) 5-pentafluorophenyl-1,2,4-oxadiazoles is reported. Irradiation of 3-pentafluorobenzoylamino-4-methyl-1,2,5-oxadiazole (Furazan) at 254 nm in methanol and in the presence of ammonia, primary or secondary aliphatic amines produces 3-amino-, 3-( N -alkylamino)-, 3-( N , N -dialkylamino)-5-pentafluorophenyl-1,2,4-oxadiazoles. The photoreaction follows the fragmentation pattern of the furazan ring with the extrusion of acetonitrile and the formation of a counterpart fragment which the nitrogen nucleophile will capture. Depending on the nature of the reagent, displacement of a fluoride anion at the C(5…

ChemInform Abstract: Synthesis of Trifluoromethylated 2-Benzoyl- and 2-Aminoimidazoles from Ring Rearrangement of 1,2,4-Oxadiazole Derivatives.

2008

Abstract Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5-phenyl-1,2,4-oxadiazole with fluorinated β-dicarbonyl compounds and subsequent base-induced Boulton–Katritzky Rearrangement (BKR) of the isolated β-enaminocarbonyl intermediate. Alternatively, one-pot reactions performed in the presence of Montmorillonite K10 favoured the condensation at the 3-amino moiety of the oxadiazole and, in some cases, allowed the direct synthesis of 2-benzoylamino-imidazoles. Hydrolysis of 2-benzoylamino-imidazoles easily yielded fluorinated 2-amino-imidazoles targets.

ChemInform Abstract: Exploiting the CNC Side Chain in Heterocyclic Rearrangements: Synthesis of 4(5)-Acylamino-imidazoles.

2010

A new variation on the Boulton-Katritzky reaction is reported, namely, involving use of a CNC side chain. A novel Montmorillonite-K10 catalyzed nonreductive transamination of a 3-benzoyl-1,2,4-oxadiazole afforded a 3-(alpha-aminobenzyl)-1,2,4-oxadiazole, which was condensed with benzaldehydes to afford the corresponding imines. In the presence of strong base, these imines underwent Boulton-Katritzky-type rearrangement to afford novel 4(5)-acylaminoimidazoles.

Heterocyclic Rearrangements: An Expedient Route to the Synthesis of Fluorinated Heterocyclic Compounds‡‡Financial support through the Italian MIUR an…

2003

Strategies against nonsense: oxadiazoles as translational readthrough-inducing drugs (TRIDs)

2019

This review focuses on the use of oxadiazoles as translational readthrough-inducing drugs (TRIDs) to rescue the functional full-length protein expression in mendelian genetic diseases caused by nonsense mutations. These mutations in specific genes generate premature termination codons (PTCs) responsible for the translation of truncated proteins. After a brief introduction on nonsense mutations and their pathological effects, the features of various classes of TRIDs will be described discussing differences or similarities in their mechanisms of action. Strategies to correct the PTCs will be presented, particularly focusing on a new class of Ataluren-like oxadiazole derivatives in comparison …

Concurrent removal of Cr(III), Cu(II), and Pb(II) ions from water by multifunctional TiO2/Alg/FeNPs beads

2019

Abstract The use of multifunctional materials for water remediation is a modern approach where adsorption phenomena and heterogeneous photocatalysis can be applied for the removal of pollutants. Since the ideal remediation system should be able to remove both organic and inorganic pollutants, a crucial aspect to consider is the knowledge of operational parameters affecting the removal process, especially when heavy metal ions are present in concoction as in real systems. Given the proven efficiency of multifunctional TiO2/Alg/FeNPs magnetic beads for the removal of model organic pollutants, this study investigated the possibility to exploit such system also for the removal of mixed heavy me…

Bioaccumulation, Biodistribution, Toxicology and Biomonitoring of Organofluorine Compounds in Aquatic Organisms

2021

This review is a survey of recent advances in studies concerning the impact of poly- and perfluorinated organic compounds in aquatic organisms. After a brief introduction on poly- and perfluorinated compounds (PFCs) features, an overview of recent monitoring studies is reported illustrating ranges of recorded concentrations in water, sediments, and species. Besides presenting general concepts defining bioaccumulative potential and its indicators, the biodistribution of PFCs is described taking in consideration different tissues/organs of the investigated species as well as differences between studies in the wild or under controlled laboratory conditions. The potential use of species as bioi…

Heat Shock Proteins in Alzheimer’s Disease: Role and Targeting

2018

Among diseases whose cure is still far from being discovered, Alzheimer’s disease (AD) has been recognized as a crucial medical and social problem. A major issue in AD research is represented by the complexity of involved biochemical pathways, including the nature of protein misfolding, which results in the production of toxic species. Considering the involvement of (mis)folding processes in AD aetiology, targeting molecular chaperones represents a promising therapeutic perspective. This review analyses the connection between AD and molecular chaperones, with particular attention toward the most important heat shock proteins (HSPs) as representative components of the human chaperome: Hsp60,…

AEROBIC 1,2-DICHLOROETHANE DEGRADERS IN CONTAMINATED GROUNDWATER

2022

ChemInform Abstract: Photoinduced Molecular Rearrangements. Some Comments on the Ring-Photoisomerization of 1,2,4-Oxadiazoles into 1,3,4-Oxadiazoles.

2010

The ring-photoisomerization of 3-amino- and 3-methylamino-5-phenyl-1,2,4-oxadiazoles into the corresponding 2-amino- and 2-methylamino-5-phenyl-1,3,4-oxadiazoles has been reinvestigated by examining the effect of a base on the photoreaction. On irradiating at λ = 254 nm in methanol, yields of the ring-photoisomers were found to be significantly enhanced by the addition of triethylamine (TEA) in the photoreaction medium. By contrast, irradiation of the 3-amino-5-phenyloxadiazole in acetonitrile containing TEA gave an almost complete photoreduction into benzoylguanidine, while few percent of the ring photoisomer were detected. Furthermore, the pyrene-sensitized photolysis of 3-amino-5-phenylo…

ChemInform Abstract: Tandem Reactions of 1,2,4-Oxadiazoles with Allylamines.

2011

Two novel thermal rearrangements are presented: the addition of allylamine (II) to oxadiazoles proceeds via ring-opening followed by cycloaddition.

Prevalence of high molecular weight apoprotein(a) isoforms in subjects with very low plasma levels of Lipoprotein(a)

2000

Synthesis, antiproliferative activity, and in silico insights of new 3-benzoylamino-benzo[ b ]thiophene derivatives

2014

A new series of 3-benzoylamino-5-imidazol-5-yl-benzo[b]thiophenes and the parent amino derivatives were synthesized and screened as antitumor agents. All tested compounds showed concentration-dependent antiproliferative activity profile against HeLa cell line, exhibiting GI50 values in the low micromolar range. The most active compounds were tested in cell cycle perturbation experiments. A rapid accumulation of cells in the G2/M phase, with a concomitant reduction of cells in both the S and G0/G1 phases, was observed, suggesting that cell exposure to selected derivatives produces mitotic failure. To rationalize the biological results, the 3-benzoylamino-benzo[b]thiophenes were analyzed thro…

Rescuing the CFTR protein function: Introducing 1,3,4-oxadiazoles as translational readthrough inducing drugs.

2018

Nonsense mutations in the CFTR gene prematurely terminate translation of the CFTR mRNA leading to the production of a truncated protein that lacks normal function causing a more severe form of the cystic fibrosis (CF) disease. About 10% of patients affected by CF show a nonsense mutation. A potential treatment of this alteration is to promote translational readthrough of premature termination codons (PTCs) by Translational Readthrough Inducing Drugs (TRIDs) such as PTC124. In this context we aimed to compare the activity of PTC124 with analogues differing in the heteroatoms position in the central heterocyclic core. By a validated protocol consisting of computational screening, synthesis an…

Theoretical study of photoinduced ring-isomerization in the 1,2,4-oxadiazole series

2004

Abstract A theoretical study of photoinduced ring-isomerization of 3-amino-5-methyl- and 3-amino-5-phenyl-1,2,4-oxadiazoles is reported. The results well agree with the reported experimental data: in particular, they explain the ring-photoisomerization into the corresponding 2-amino-1,3,4-oxadiazoles through a ring contraction-ring expansion route; moreover, the occurrence of competing pathways involving both the ring contraction and the internal cyclization–isomerization mechanism during irradiation of the 5-alkyl substituted substrates in the presence of a base has been also substantiated.

Hydration/elimination reactions of trapped protonated fluoroalkyl triazines

2007

Uno studio comparativo in silico sui possibili target di Ataluren e analoghi farmaci promotori di readthrough di codoni di stop prematuri

2019

E’ noto in letteratura che Ataluren (acido 5-(fluorofenil)-1,2,4-ossadiazolil-benzoico) sia in grado di sopprimere le mutazioni non senso favorendo il readthrough dei codoni di stop prematuri, anche se il suo meccanismo di azione non risulta ancora chiaro. La probabile interazione tra Ataluren e CTFR-mRNA è stata precedentemente studiata mediante dinamica molecolare. In questo studio1, abbiamo esteso il modeling del probabile meccanismo di azione di Ataluren mediante approcci computazionali completementari, quali Induced Fit Docking (IFD), Quantum Polarized Ligand Docking (QPLD), metodi MM-GBSA e mutagenesi computazionale. Oltre a considerare il CTFR-mRNA, sono stati presi in considerazione…

ChemInform Abstract: Photoinduced Single Electron Transfer on 5-Aryl-1,2,4-oxadiazoles: Some Mechanistic Investigations in the Synthesis of Quinazoli…

2010

The photochemistry of some 5-aryl-3-methoxy- (or 5-aryl-3-phenyl-) 1,2,4-oxadiazoles irradiated in the presence of different sensitizers [such as diphenylacetylene (DAC), 9,10-diphenylanthracene (DAN), or triphenylene (TPH)] or ground-state donors such as triethylamine (TEA) has been investigated. Intermediates arising from breaking of the ring O-N bond develop both into quinazolin-4-ones (by a heterocyclization reaction involving the aryl at the C-5 of the oxadiazole nucleus) and into open-chain products (corresponding to a reduction at the ring O-N bond), in different ratios depending on their structures and photoreaction conditions. A reasonable explanation considers sensitization by pho…

Can phthalates move into the eggs of the loggerhead sea turtle Caretta caretta? The case of the nests on the Linosa Island in the Mediterranean Sea

2021

During the monitoring of Caretta caretta nests on the island of Linosa, 30 unhatched eggs from four nests were collected to study the presence of phthalates in their three components (shell, yolk, and albumen). Four phthalates, namely diethyl (DEP), dibutyl (DBP), di-(2-ethylhexyl) (DEHP), and dioctyl (DOTP) phthalic acid esters (PAE), which are widely used as additives in plastics, were detected in all egg components. The most frequently found phthalate was DBP, followed by DEHP in eggshell and yolk. Dimethyl- (DMP) and butylbenzyl-phthalate (BBP) were below the limits of detection for all samples. The high total phthalate recorded in the yolk suggests that contamination could arise by vit…

Photooxidations of Alkenes in Fluorinated Constrained Media:  Fluoro-organically Modified NaY as Improved Reactors for Singlet Oxygen “Ene” Reactions

2007

Creating a stationary fluorinated environment inside the zeolite cavity can increase the reactivity observed for intrazeolite photooxidation of alkenes. Exchanging the zeolite with fluorinated organic cations is a much more effective strategy than simply using a fluorinated solvent for slurry irradiations. Use of cations containing C-F bonds is also more efficient than use of deuterated cations for creation of a singlet oxygen friendly environment where the quenching processes are slowed down. Doping the zeolite with fluoro-organic cation 4 resulted in an increase in the singlet oxygen lifetime to 12 micros.

Pharmacophore-Based Design of New Chemical Scaffolds as Translational Readthrough-Inducing Drugs (TRIDs)

2020

[Image: see text] Translational readthrough-inducing drugs (TRIDs) rescue the functional full-length protein expression in genetic diseases, such as cystic fibrosis, caused by premature termination codons (PTCs). Small molecules have been developed as TRIDs to trick the ribosomal machinery during recognition of the PTC. Herein we report a computational study to identify new TRID scaffolds. A pharmacophore approach was carried out on compounds that showed readthrough activity. The pharmacophore model applied to screen different libraries containing more than 87000 compounds identified four hit-compounds presenting scaffolds with diversity from the oxadiazole lead. These compounds have been s…

Fluoro heterocycles. A photochemical methodology for the synthesis of 3-amino- and 3-(N-alkylamino)-5-perfluoroalkyl-1,2,4-oxadiazoles

2000

Abstract A photochemical methodology for the synthesis of perfluoroalkyl-1,2,4-oxadiazoles has been described. 3-Amino- and 3-( N -alkylamino)-5-perfluoroalkyl-1,2,4-oxadiazoles have been prepared by irradiation of 3-perfluoroalkanoylamino-4-phenyl-1,2,5-oxadiazoles (furazans) at λ =313 nm in methanol and in the presence of ammonia or primary aliphatic amines.

Inhibition of FTSJ1, a tryptophan tRNA-specific 2’-O-methyltransferase as possible mechanism to readthrough premature termination codons (UGAs) of th…

2022

Cystic Fibrosis (CF) is an autosomal recessive genetic disease caused by mutations in the CFTR gene, coding for the CFTR chloride channel. About 10 % of the mutations affecting the CFTR gene are "stop" mutations, which generate a Premature Termination Codon (PTC), thus resulting in the synthesis of a truncated CFTR protein. A way to bypass PTC relies on ribosome readthrough, that is the capacity of the ribosome to skip a PTC, thus generating a full-length protein. “TRIDs” are molecules exerting ribosome readthrough and for some of them the mechanism of action is still under debate. By in silico analysis as well as in vitro studies, we investigate a possible mechanism of action (MOA) by whic…

Curcumin Affects HSP60 Folding Activity and Levels in Neuroblastoma Cells.

2020

The fundamental challenge in fighting cancer is the development of protective agents able to interfere with the classical pathways of malignant transformation, such as extracellular matrix remodeling, epithelial−mesenchymal transition and, alteration of protein homeostasis. In the tumors of the brain, proteotoxic stress represents one of the main triggering agents for cell transformation. Curcumin is a natural compound with anti-inflammatory and anti-cancer properties with promising potential for the development of therapeutic drugs for the treatment of cancer as well as neurodegenerative diseases. Among the mediators of cancer development, HSP60 is a key factor for the maintenance of…

Photodegradation of selected phthalates on mural painting surfaces under UV light irradiation

2014

Abstract The esters of phthalic acid are considered as hazardous pollutants due to their mutagenicity, carcinogenicity and are also classified as endocrine disruptor chemicals. Several compounds of this class of substances for decades, and probably even now, were used as softeners in water-based synthetic paintings. Surfaces and structures, such as house walls painted with phthalates based paintings, can be a concern to construction workers engaged in demolition, restore and paint removal activities if they are not protected from hazardous dust inhalation. In this paper we report the results of an investigation about phthalate ester degradation by direct UV irradiation at 254 nm. The result…

Modulating disease-relevant tau oligomeric strains by small molecules

2020

The pathological aggregation of tau plays an important role in Alzheimer's disease and many other related neurodegenerative diseases, collectively referred to as tauopathies. Recent evidence has demonstrated that tau oligomers, small and soluble prefibrillar aggregates, are highly toxic due to their strong ability to seed tau misfolding and propagate the pathology seen across different neurodegenerative diseases. We previously showed that novel curcumin derivatives affect preformed tau oligomer aggregation pathways by promoting the formation of more aggregated and nontoxic tau aggregates. To further investigate their therapeutic potential, we have extended our studies o disease-relevant bra…

Tryptophan catabolism via kynurenine production in Streptomyces coelicolor: identification of three genes coding for the enzymes of tryptophan to ant…

2011

Most enzymes involved in tryptophan catabolism via kynurenine formation are highly conserved in Prokaryotes and Eukaryotes. In humans, alterations of this pathway have been related to different pathologies mainly involving the central nervous system. In Bacteria, tryptophan and some of its derivates are important antibiotic precursors. Tryptophan degradation via kynurenine formation involves two different pathways: the eukaryotic kynurenine pathway, also recently found in some bacteria, and the tryptophan-to-anthranilate pathway, which is widespread in microorganisms. The latter produces anthranilate using three enzymes also involved in the kynurenine pathway: tryptophan 2,3-dioxygenase (TD…

New potent antibacterials against Gram-positive multiresistant pathogens: effects of side chain modification and chirality in linezolid-like 1,2,4-ox…

2014

The effects of side chain modification and chirality in linezolid-like 1,2,4-oxadiazoles have been studied to design new potent antibacterials against Gram-positive multidrug-resistant pathogens. The adopted strategy involved a molecular modelling approach, the synthesis and biological evaluation of new designed compounds, enantiomers separation and absolute configuration assignment. Experimental determination of the antibacterial activity of the designed (S)-1-((3-(4-(3-methyl-1,2,4-oxadiazol-5- yl)phenyl)-oxazolidin-2-one-5-yl)methyl)-3-methylthiourea and (S)-1-((3-(3-fluoro-4-(3-methyl-1,2,4- oxadiazol-5-yl)phenyl)-oxazolidin-2-one-5-yl)methyl)-3-methylthiourea against multidrug resistan…

A Novel Zeolite-Induced Population of a Planar Viologen Conformation. New Viologen Charge Transfer Complexes and Alkene/Viologen/Zeolite Arrays

2004

A rare example of a novel zeolite-induced conformational change and a mechanism for this process are suggested in order to rationalize an unexpected spontaneous intrazeolite reduction observed during preparation of a new viologen (MQ2+)-doped zeolite (NaY). In addition, the formations of six new alkene/viologen/ zeolite charge transfer (CT) arrays using NaMQY and the previously reported NaMVY are also reported. The binding constants between MQ2+ and MV2+ and 2,3-dimethyl-2-butene (TME) were determined using the Benesi-Hildebrand approach, and the stabilities of these CT complexes are compared to their intrazeolite analogue.

Discrimination of almonds (Prunus dulcis) geographical origin by minerals and fatty acids profiling

2016

Twenty-one almond samples from three different geographical origins (Sicily, Spain and California) were investigated by determining minerals and fatty acids compositions. Data were used to discriminate by chemometry almond origin by linear discriminant analysis. With respect to previous PCA profiling studies, this work provides a simpler analytical protocol for the identification of almonds geographical origin. Classification by using mineral contents data only was correct in 77% of the samples, while, by using fatty acid profiles, the percentages of samples correctly classified reached 82%. The coupling of mineral contents and fatty acid profiles lead to an increased efficiency of the clas…

Five-to-Six Membered Ring-rearrangements in the Reaction of 5-Perfluoroalkyl-1,2,4-oxadiazoles with Hydrazine and Methylhydrazine

2006

The hydrazinolysis reaction of 5-perfluoroalkyl-1,2,4-oxadiazoles with hydrazine or methylhydrazine as bidentate nucleophiles has been investigated. The reaction occurred through the addition of the bidentate nucleophile to the C(5)-N(4) double bond of the 1,2,4-oxadiazole followed by ring-opening and ring-closure (ANRORC) involving the second nucleophilic site of the reagent. This ring-closure step could involve either the original C(3) of the 1,2,4-oxadiazole (giving a five-to-five membered ring rearrangement) or an additional electrophilic center linked to it (exploiting a five-to-six membered ring rearrangement). An alternative initial nucleophilic attack may involve the additional elec…

Lower rim arylation of calix[n]arenes with extended perfluorinated domains

2006

Abstract Exhaustive O-arylation of p-tert -butylcalix[ n ]arenes 2 ( n  = 4–8) with an excess of 3-pentadecafluoroheptyl-5-pentafluorophenyl-1,2,4-oxadiazole 3 and K 2 CO 3 in refluxing acetonitrile provides an easy entry to a new family of perfluorinated calix[ n ]arenes 1 . The cyclic tetramer furnishes a mixture of cone , partial cone , and 1,2-alternate conformers, while the larger macrocycles afford single products. The structures of all new compounds are substantiated by NMR techniques and MALDI-TOF mass spectral data. Single-crystal X-ray diffraction studies on the pentamer derivative 1b reveal a distorted cone-in conformation of the calixarene cup.

Synthesis and characterization of a series of alkyl-oxadiazolylpyridinium salts as perspective ionic liquids

2007

The synthesis of a series of 1,2,4-oxadiazolyl-N-methylpyridinium salts differing in the length and the position of the alkyl chain in the heterocyclic ring and the counter ions is reported. Some features of this new family of salts as perspective ionic liquids are described and the influence of the varying moieties in the modulation of the properties is discussed.

Synthesis of 4(5)-phenacyl-imidazoles from isoxazole side-chain rearrangements

2010

A novel base-induced rearrangement of isoxazoles into imidazole derivatives is reported. In the isoxazole series, this represents the first example of a three-atom side-chain rearrangement involving a CNC sequence. The reactions are carried out under nitrogen and produced 2-aryl-4(5)-phenacyl-5(4)-phenyl-imidazoles in high yields. In the presence of oxygen, a cascade rearrangement-oxidation reaction sequence was observed and imidazole derivatives bearing an oxidized side-chain were isolated.

Experimental and DFT Studies on Competitive Heterocyclic Rearrangements. Part 2:1 A One-Atom Side-Chain versus the Classic Three-Atom Side-Chain (Bou…

2007

The experimental investigation of the base-catalyzed rearrangements of 3-acylamino-1,2,4-oxadiazoles evidenced a new reaction pathway which competes with the well-known ring-degenerate Boulton-Katritzky rearrangement (BKR). The new reaction consists of a one-atom side-chain rearrangement that is base-activated, occurs at a higher temperature than the BKR, and irreversibly leads to the corresponding 2-acylamino-1,3,4-oxadiazoles. An extensive DFT study is reported to elucidate the proposed reaction mechanism and to compare the three possible inherent routes: (i) the reversible three-atom side-chain ring-degenerate BKR, (ii) the ring contraction-ring expansion route (RCRE), and (iii) the one-…

Neutral solar photo-Fenton degradation of 4-nitrophenol on iron-enriched hybrid montmorillonite-alginate beads (Fe-MABs)

2014

Hybrid montmorillonite-alginate beads (MABs) were prepared by the ion-gelation method from alginate and montmorillonite clay suspension dropped in a calcium chloride solution. Similarly, iron-enriched beads (Fe-MABs) were prepared using iron-exchanged montmorillonite. All beads were characterized by atomic absorption and Fourier-transform infrared spectroscopy. The efficiency of Fe-MABs as catalysts for the solar photo-Fenton performed at initial pH = 7.0 was evaluated by varying the catalyst amount and hydrogen peroxide concentration, and monitoring the removal of 4-nitrophenol (4-NP) at initial concentration of 10 ppm. A kinetic analysis showed that the removal of 4-NP by Fe-MABs followed…

Recent development in fluorinated antibiotics

2019

This chapter presents the most recent results in the development of fluorinated antibioticsby taking into consideration modern challenges of multidrug-resistant pathogens. After a brief introduction on the direct and indirect effects of fluorine and fluorinated moieties in regulating biological activity, the chapter is developed in three main subsections discussing the two major classes of fluorinated antibiotics, fluoroquinolones and oxazolidinones, plus an overview of recent research on the antibiotic activity of fluorinated analogs of tetracyclines, peptidomimetics, triazoles, and nucleosides. Discussed aspects include: (1) Synthesis and challenges posed by the introduction of fluorinate…

Synthesis of Heteroaromatics via Rearrangement Reactions

2010

Combined Adsorption/Photocatalytic dye removal by copper-titania-fly ash composite

2020

Abstract Achieving both photocatalytic efficiency and adsorption capacity is essential to produce a highly efficient photocatalyst. This study fabricated a new photocatalyst by combining copper (Cu) doped titanium dioxide (TiO2) with fly ash (FA). The photocatalysts were synthesized using mild acid (acid-FA/Cu/TiO2), base (base-FA/Cu/TiO2), and deionized water (rFA/Cu/TiO2) activated FA. EDX confirmed the inclusion of Cu in both Cu/TiO2 and FA/Cu/TiO2 composites. XRD analysis indicated the presence of the anatase form of TiO2 after Cu doping and incorporation into modified FA. All three FA/Cu/TiO2 composites demonstrated high absorption (UV and visible region) compared to their TiO2 and Cu/…

Experimental and DFT Studies on Competitive Heterocyclic Rearrangements. 3. A Cascade Isoxazole−1,2,4-Oxadiazole−Oxazole Rearrangement

2008

The thermal rearrangements of 3-acylamino-5-methylisoxazoles 1 have been investigated under basic and neutral conditions and interpreted with the support of computational data. The density functional theory (DFT) study on the competitive routes available for the base-catalyzed thermal rearrangement of isoxazoles 1 showed that the Boulton-Katritzky (BK) rearrangement, producing the less stable 3-acetonyl-1,2,4-oxadiazoles 5, is a much more favored process than either the migration-nucleophilic attack-cyclization (MNAC) or the ring contraction-ring expansion (RCRE). In turn, an increase in reaction temperature will promote the MNAC of oxadiazoles 5, producing the more stable 2-acylaminooxazol…

Photoinduced Single Electron Transfer on 5-Aryl-1,2,4-oxadiazoles:  Some Mechanistic Investigations in the Synthesis of Quinazolin-4-ones

1999

The photochemistry of some 5-aryl-3-methoxy- (or 5-aryl-3-phenyl-) 1,2,4-oxadiazoles irradiated in the presence of different sensitizers [such as diphenylacetylene (DAC), 9,10-diphenylanthracene (DAN), or triphenylene (TPH)] or ground-state donors such as triethylamine (TEA) has been investigated. Intermediates arising from breaking of the ring O-N bond develop both into quinazolin-4-ones (by a heterocyclization reaction involving the aryl at the C-5 of the oxadiazole nucleus) and into open-chain products (corresponding to a reduction at the ring O-N bond), in different ratios depending on their structures and photoreaction conditions. A reasonable explanation considers sensitization by pho…

Fluorinated Heterocyclic Compounds. A Photochemical Approach to a Synthesis of Fluorinated Quinazolin-4-ones

2004

An efficient and generalized photochemical methodology for the preparation of fluorinated quinazolin-4-ones is described. Depending on the starting substrate, quinazolin-4-ones bearing a perfluoroalkyl- or perfluoroaryl- substituent in position 2 or fluorine atoms on any positions of the benzo-fused moiety can easily be obtained. 5-Aryl-3-perfluoroalkylpentafluorophenyl- or 5-polyfluoroaryl-3-phenyl(methyl)-1,2,4-oxadiazoles, respectively, can be considered as ideal precursors that can be transformed into the target quinazolin-4-ones by irradiation in the presence of triethylamine (TEA) (at λ = 313 nm) or pyrene (at λ = 365 nm) in dry methanol or acetonitrile as solvent. Some mechanistic co…

Photochemically Produced Singlet Oxygen: Applications and Perspectives

2018

This Review aims to provide early stage researchers with an updated guide to applications of photochemically produced singlet oxygen and, at the same time, widen the experienced researcher's perspectives in a holistic approach to singlet oxygen chemistry. Without being exhaustive, literature between 2010 and early 2018 has been surveyed by focusing on a critical evaluation of new knowledge and applications. After an introductory section concerning singlet oxygen production, detection, and interactions with biological systems, subsequent sections describe current applications of singlet-oxygen-enabled technology. Besides strictly chemical synthesis applications, attention has been given to t…

Mesomorphic and electrooptical properties of viologens based on non-symmetric alkyl/polyfluoroalkyl functionalization and on an oxadiazolyl-extended …

2019

Two different sets of ionic liquid crystals based on bistriflimide salts of non-symmetrically substituted polyfluorinated bipyridinium (viologens) and bent symmetrically substituted dialkyl-oxadiazolyl-bipyridinium have been synthesized, in order to study the effect on the mesomorphic and electrooptical properties of the non-symmetric functionalization (alkyl chain and fluoroalkyl chains of different lengths) on the two pyridinium rings and additionally the effect of a bent conjugated spacer among the two pyridinium units of the viologen. POM and DSC characterization show that the synthesized salts have a mesomorphic and, in some cases, polymesomorphic behaviour in a wide thermal range, als…

Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles

2010

The reaction of various 1,2,4-oxadiazoles with an excess of hydrazine in DMF has been investigated. 3-Amino- 1,2,4-triazoles are produced through a reductive ANRORC pathway consisting of the addition of hydrazine to the 1,2,4-oxadiazole followed by ring-opening, ring-closure, and final reduction of the 3-hydroxylamino-1,2,4-triazole intermediate. The general applicability of 1,2,4-oxadiazoles ANRORC reactivity is demonstrated also in the absence of C(5)-linked electron-withdrawing groups.

Oxadiazolyl-pyridines and perfluoroalkyl-carboxylic acids as building blocks for protic ionic liquids: crossing the thin line between ionic and hydro…

2012

A series of 18 samples has been prepared in order to obtain fluorinated materials as Protic Ionic Liquids (PILs). These were synthesized by appropriately mixing 1,2,4-oxadiazoles derivatised with two pyridines, or one pyridine and a fluorinated chain, and perfluoroalkyl-carboxylic acids, either mono- or dicarboxylic, leading to symmetric and non-symmetric materials. Many of them showed low melting points. However, the possibility of classifying the synthesized materials as PILs is discussed in terms of effective ionicity of the systems by the combination of Density Functional Theory (DFT) calculation and IR spectroscopy. The important outcome of our investigation is that the complete proton…

Exploring the readthrough of nonsense mutations by non-acidic Ataluren analogues selected by ligand-based virtual screening

2016

Abstract Ataluren, also known as PTC124, is a 5-(fluorophenyl)-1,2,4-oxadiazolyl-benzoic acid suggested to suppress nonsense mutations by readthrough of premature stop codons in the mRNA. Potential interaction of PTC124 with mRNA has been recently studied by molecular dynamics simulations highlighting the importance of H-bonding and stacking π−π interactions. A series of non-acidic analogues of PTC124 were selected from a large database via a ligand-based virtual screening approach. Eight of them were synthesized and tested for their readthrough activity using the Fluc reporter harboring the UGA premature stop codon. The most active compound was further tested for suppression of the UGA non…

Mild Aerobic Exercise Training Hardly Affects the Diaphragm ofmdxMice

2017

In the mdx mice model of Duchenne Muscular Dystrophy (DMD), mild endurance exercise training positively affected limb skeletal muscles, whereas few and controversial data exist on the effects of training on the diaphragm. The diaphragm was examined in mdx (C57BL/10ScSn-Dmdmdx) and wild-type (WT, C57BL/10ScSc) mice under sedentary conditions (mdx-SD, WT-SD) and during mild exercise training (mdx-EX, WT-EX). At baseline, and after 30 and 45 days (training: 5 d/wk for 6 weeks), diaphragm muscle morphology and Cx39 protein were assessed. In addition, tissue levels of the chaperonins Hsp60 and Hsp70 and the p65 subunit of nuclear factor-kB (NF-kB) were measured in diaphragm, gastrocnemius, and q…

Synthesis of Fluorinated Bent-Core Mesogens (BCMs) Containing the 1,2,4-Oxadiazole Ring

2015

New fluorinated bent-core mesogens containing the 1,2,4-oxadiazole or 1,2,4-triazole nucleus have been synthesized taking advantage of the ANRORC (Addition of Nucleophile, Ring-Opening, Ring-Closure) reactivity of 5-perfluoroalkyl-1,2,4-oxadiazoles. Physical state changes of the obtained compounds were characterized through DSC, POM, and SAXS. Besides the formation of a smectic mesophase, a novel behavior as organic molecular glass was evidenced for some 1,2,4-oxadiazole derivatives.

Synthesis and mesomorphism of related series of triphilic ionic liquid crystals based on 1,2,4-triazolium cations

2021

Abstract The synthesis, liquid crystal and conductivity properties of a series of 27 salts based on the 5-(4-(alkyloxy)phenyl)-1,2,4-triazol-4-ium cation bearing a perfluoroalkyl chain with triflate, tetrafluoroborate and bistriflimide anion are reported. The cations are regarded as triphilic on account of their three distinct regions – hydrocarbon, fluorocarbon and ionic. The mesophases were characterised by a combination of polarised optical microscopy, calorimetry and small-angle scattering experiments using both X-rays and neutrons, while thermal stability was probed using thermogravimetric analysis. The liquid crystal properties are found to be dependent on the anion and the length of …

Toxic Tau Oligomers Modulated by Novel Curcumin Derivatives

2019

AbstractThe pathological aggregation and accumulation of tau, a microtubule-associated protein, is a common feature amongst more than 18 different neurodegenerative diseases that are collectively known as tauopathies. Recently, it has been demonstrated that the soluble and hydrophobic tau oligomers are highly toxic in vitro due to their capacity towards seeding tau misfolding, thereby propagating the tau pathology seen across different neurodegenerative diseases. Modulating the aggregation state of tau oligomers through the use of small molecules could be a useful therapeutic strategy to target their toxicity, regardless of other factors involved in their formation. In this study, we screen…

Molecular rearrangements of 1-oxa-2-azoles as an expedient route to fluorinated heterocyclic compounds

2005

Molecular rearrangements of O-N bond-containing azoles (1-oxa-2- azoles) represent a wide class of reactions by which various heterocycle-to- heterocycle transformations can be performed as alternative synthetic methodologies. The material presented in this review is an extensive survey of both thermal and photochemical methodologies that have been applied to fluorinated oxadiazoles, and shows how molecular rearrangements can be an alternative and in some cases the most convenient route for the synthesis of several fluorinated heterocycles.

Designing fluorous domains. Synthesis of a series of pyridinium salts bearing a perfluoroalkylated azole moiety

2006

The synthesis of a series of N-methylpyridinium salts bearing a perfluoroalkylated 1,2,4-oxadiazole or 1,2,4-triazole moiety is reported. X-Ray structures of representative perfluoroalkyl-triazolylpyridine (15) and methyl- pyridinium iodide salt (5a) are reported. Their crystal packing clearly shows segregation between the aromatic and parallel double layer fluorinated regions.

Synthesis of Fluorinated Indazoles Through ANRORC-Like Rearrangement of 1,2,4-Oxadiazoles with Hydrazine.

2006

A series of 6-substituted fluorinated indazoles has been obtained through an ANRORC-like rearrangement (Addition of Nucleophile, Ring-Opening and Ring-Closure) of 5-tetrafluorophenyl-1,2,4-oxadiazoles with hydrazine. The initial addition of the bidentate nucleophile to the electrophilic C(5) of the 1,2,4-oxadiazole ring, followed by ring opening and ring closure, leads to the formation of fluorinated indazoles in high yield under mild experimental conditions. Functionalization of the C(6) in the final indazole nucleus was preliminarily achieved through a nucleophilic aromatic substitution on the starting 5-pentafluorophenyl-1,2,4-oxadiazole.

Escherichia coli inactivation by neutral solar heterogeneous photo-Fenton (HPF) over hybrid iron/montmorillonite/alginate beads

2015

Abstract Hybrid alginate montmorillonite iron enriched beads (Fe-MABs) were synthesized using ion gelation method and used as catalyst in Escherichia coli inactivation in neutral solar photo-Fenton conditions. A kinetic analysis showed that the E. coli inactivation by Fe-MABs followed a pseudo first-order kinetics model. Complete disinfection was achieved in 1 h of irradiation by using Fe-MABs in the presence of 10 ppm of H 2 O 2 . Preliminary studies on recyclability showed possible beads reused up to four times. Overall, Fe-MABs represent an environmental friendly material able to achieve bactericidal performance measured by E. coli inactivation under photooxidative conditions.

OXADIAZOLE DERIVATIVES FOR THE TREATMENT OF GENETIC DISEASES DUE TO NONSENSE MUTATIONS

2018

Are disclosed oxadiazole derivatives, their use as medicaments and in particular for the treatment of diseases associated with the presence of a nonsense mutation in the gene or a premature stop codon in the mRNA, pharmaceutical formulation comprising said oxadiazole derivatives and prodrug or mixture thereof and the methods for the preparation of said Oxadiazole derivatives.

Study on the thermotropic properties of highly fluorinated 1,2,4-oxadiazolylpyridinium salts and their perspective applications as ionic liquid cryst…

2007

A new series of fluorinated salts, iodides and trifluoromethanesulfonates, was synthesized from perfluoroalkylated 1,2,4-oxadiazolylpyridines. Their thermotropic properties were investigated by combined temperature resolved small angle and wide angle X-ray scattering, differential scanning calorimetry and polarised optical microscopy. The UV–visible and photoluminescence properties were studied for all compounds. The results showed for two compounds the existence of an enantiotropic mesomorphic smectic liquid crystal phase. All iodides showed thermochromism phenomena suggesting prospective applications in optoelectronics.

The Binding Mechanism of Epolactaene to Hsp60 Unveiled by in Silico Modelling

2016

Molecular Dynamics (MD) simulations and DFT/MM calculations were performed in order to rationalize available experimental results and to provide structural details on the binding mechanism of Epolactaene (EPO) to the 60 KDa Heat Shock Protein (Hsp60). The available crystal structure of Hsp60 represents the last step of the chaperone folding cycle, while the Hsp60-EPO complex was obtained by using a homology model of Hsp60, in order to simulate a state related to the beginning of the folding cycle (Rs1). The results of MD simulations point out that EPO shows the highest binding affinity for the empty ATP binding site. The presence of ATP opens a channel that allows the entrance of both EPO d…

The synthesis of fluorinated heteroaromatic compounds. Part 1. Five-membered rings with more than two heteroatoms. A review

2005

(2005). THE SYNTHESIS OF FLUORINATED HETEROAROMATIC COMPOUNDS. PART 1. FIVE-MEMBERED RINGS WITH MORE THAN TWO HETEROATOMS. A REVIEW. Organic Preparations and Procedures International: Vol. 37, No. 5, pp. 447-506.

Tandem Reactions of 1,2,4-Oxadiazoles with Allylamines

2011

A reaction of 3-chloro-1,2,4-oxadiazoles with allylamine and diallylamine has been investigated. 3,3a,4,5-Tetrahydroisoxazolo[3,4-d]pyrimidines are produced through a tandem ANRORC/[3 + 2]cycloaddition pathway consisting of the addition of allylamine to the 1,2,4-oxadiazole, followed by ring opening, nitrone formation, and finally cycloaddition. 3-N-Allylamino-1,2,4-oxadiazoles were also obtained as minor products through a classical SNAr. Conversely, a reaction with diallylamine produces 3-N,N-diallylamino-1,2,4-oxadiazole and imidazoline through tandem SNAr/aziridination and nucleophilic ring opening.

Readthrough Inducing Drugs (TRIDs) in human fibroblasts harboring the c.5047 C>T (R1683*) nonsense mutation

2022

ChemInform Abstract: 1,2,4-Oxadiazole Rearrangements Involving an NNC Side-Chain Sequence.

2010

The thermal rearrangement of N-1,2,4-oxadiazol-3-yl-hydrazones into 1,2,4-triazole derivatives is reported. This represents the first example of a three-atom side-chain rearrangement involving an NNC sequence linked at the C(3) of the oxadiazole. The reactions carried out under solvent-free conditions produced good to high yields of the final products.

1,2,4-Oxadiazole rearrangements involving an NNC side-chain sequence.

2009

The thermal rearrangement of N-1,2,4-oxadiazol-3-yl-hydrazones into 1,2,4-triazole derivatives is reported. This represents the first example of a three-atom side-chain rearrangement involving an NNC sequence linked at the C(3) of the oxadiazole. The reactions carried out under solvent-free conditions produced good to high yields of the final products.

Toward a Rationale for the PTC124 (Ataluren) Promoted Readthrough of Premature Stop Codons: A Computational Approach and GFP-Reporter Cell-Based Assay

2014

The presence in the mRNA of premature stop codons (PTCs) results in protein truncation responsible for several inherited (genetic) diseases. A well-known example of these diseases is cystic fibrosis (CF), where approximately 10% (worldwide) of patients have nonsense mutations in the CF transmembrane regulator (CFTR) gene. PTC124 (3-(5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl)-benzoic acid), also known as Ataluren, is a small molecule that has been suggested to allow PTC readthrough even though its target has yet to be identified. In the lack of a general consensus about its mechanism of action, we experimentally tested the ability of PTC124 to promote the readthrough of premature termination c…

The effect of montmorillonite clay in alginate gel beads for polychlorinated biphenyl adsorption: Isothermal and kinetic studies

2014

Beads of alginate montmorillonite have been used as sorbent for polychlorinated biphenyls from aqueous solutions.The structure and the differences between the different beads were established by IR spectroscopy (FT-IR). The adsorption at 25 °C has been studied in a batch system, following its kinetics and assessing adsorbent dose, initial PCB concentrations, and pH effects. The results show that increasing the initial concentration of the PCBs and the adsorption time favored the adsorption. Adsorption isotherm data were modeled using Chapman, Freundlich and Langmuir adsorption isotherms and the appropriate parameters were calculated.Adsorption of trichlorobiphenyls on alginate–montmorilloni…

An analytical method for monitoring micro-traces of landfill leachate in groundwater using fluorescence excitation–emission matrix spectroscopy

2016

In this study, we use three-dimensional excitation-emission matrix (EEM) fluorescence spectroscopy for the identification of contamination of natural water bodies by landfill leachate. In particular, EEM was applied to provide information about the presence and quantities of leachate in ground waters. A good linear relationship was found between the fluorescence intensity emission of groundwater spiked with landfill leachate and the volumes of the latter, suggesting that there was no intrinsic fluorescence in the concentration range of 0-1000 μL L-1. The obtained values of the LOD (10 μL L-1; TOC = 34 μg L-1) and LOQ (34 μL L-1; TOC = 114 μg L-1) allow us to detect the presence and the amou…

1,2,4-Triazolium ions as flexible scaffolds for the construction of polyphilic ionic liquid crystals

2018

A novel scaffold for the construction of self-organised ionic liquids and ionic liquid crystals bearing both perfluorocarbon and hydrocarbon moieties has been developed. The phase behaviour and physical properties of these materials can be tuned as a function of chain length and fluorine content and significant structural elaboration is possible, giving a highly flexible system.

FLUORINATED DERIVATIVES OF A POLYASPARTAMIDE BEARING POLYETHYLENE GLYCOL CHAINS AS OXYGEN CARRIERS

2008

Abstract In this paper the synthesis and characterization of new fluorinated polymers based on a polyaspartamide bearing polyethylene glycol (PEG) chains, are reported. The starting material was the α,β-poly(N-2-hydroxyethyl)- dl -aspartamide (PHEA), a water soluble and biocompatible polymer, that has been derivatized with both polyethylene glycol (with a molecular weight of 2000 Da) and 5-pentafluorophenyl-3-perfluoroheptyl-1,2,4-oxadiazole. By varying the amount of the fluorinated oxadiazole, three samples have been prepared and characterized by FT-IR, 1H NMR, 19F NMR and UV–VIS spectroscopy. Size exclusion chromatography analysis of these copolymers revealed the occurrence of a self-asso…

1,2-DICHLOROETHANE CONTAMINATED AQUIFER: MICROBIAL COMMUNITY RESPONSE TO BIOSTIMULATION IN MICROCOSM

2022

Photochemistry of 1,2,4-oxadiazoles. A DFT study on photoinduced competitive rearrangements of 3-amino- and 3-N-methylamino-5-perfluoroalkyl-1,2,4-ox…

2006

The photoinduced competitive rearrangements of 5-perfluoroalkyl-3-amino(N-alkylamino)-1,2,4-oxadia- zoles have been investigated by DFT calculations and UV-vis spectroscopy. The observed product selectivity depends on the number of hydrogen atoms present in the amino moiety and involves two or three possible routes: (i) ring contraction-ring expansion (RCRE), (ii) internal-cyclization isomerization (ICI), or (iii) C(3)-N(2) migration-nucleophilic attack-cyclization (MNAC). UV absorption and fluorescence spectra of the reactants, and vertical excitation energy values, calculated by time dependent DFT, support the involvement of a neutral singlet excited state in the photoexcitation process. …

The synthesis of fluorinated heteroaromatic compounds. Part 2. Five-membered rings with two heteroatoms. A review

2007

Fluorinated Heterocyclic Compounds. An Expedient Route to 5-Perfluoroalkyl-1,2,4-triazoles via an Unusual Hydrazinolysis of 5-Perfluoroalkyl-1,2,4-ox…

2003

The hydrazinolysis reaction of 5-perfluoroalkyl-1,2,4-oxadiazoles has been investigated. Nucleophilic addition of the reagent to the C(5)-N(4) double bond of the oxadiazole ring, followed by ring-opening and then ring-closure involving the beta-nitrogen atom of the hydrazino moiety and the C(3) of the oxadiazole ring, explains the formation of 5-perfluoroalkyl-1,2,4-triazoles as final products. Useful applications in synthesis of this uncommon hydrazinolysis can be claimed.

Targeting Nonsense: Optimization of 1,2,4-Oxadiazole TRIDs to Rescue CFTR Expression and Functionality in Cystic Fibrosis Cell Model Systems

2020

Cystic fibrosis (CF) patients develop a severe form of the disease when the cystic fibrosis transmembrane conductance regulator (CFTR) gene is affected by nonsense mutations. Nonsense mutations are responsible for the presence of a premature termination codon (PTC) in the mRNA, creating a lack of functional protein. In this context, translational readthrough-inducing drugs (TRIDs) represent a promising approach to correct the basic defect caused by PTCs. By using computational optimization and biological screening, we identified three new small molecules showing high readthrough activity. The activity of these compounds has been verified by evaluating CFTR expression and functionality after…

Gas phase behavior of radical cations of perfluoroalkyl-1,2,4-triazines: an experimental and theoretical study

2009

Electron ionization mass spectrometry and low-energy collision-induced decomposition reactions occurring in a tridimensional ion trap, together with density functional theory (DFT) calculations on neutrals, even- and odd-electron cations, have been used to study the gas-phase ion chemistry of a series of perfluoroalkyl-1,2,4-triazines. Loss of oxygen, due to thermal degradation occurring before ionization, likely involving the hydroxylamino group, has been observed. Compounds having a carbonyl group at position 6 of the triazine ring fragment in the source by elimination of NO followed by HF or CO. The decomposition pathways occurring due to CID experiments have shown interesting features d…

Photochemistry of Fluorinated Heterocyclic Compounds. An Expedient Route for the Synthesis of Fluorinated 1,3,4-Oxadiazoles and 1,2,4-Triazoles

2004

The photochemistry of some 3-N-alkylamino-5-perfluoroalkyl-1,2,4-oxadiazoles in the presence of nitrogen nucleophiles such as ammonia and primary and secondary aliphatic amines has been investigated. The primary photolytic intermediate from the cleavage of the ring O-N bond follows two distinct and competing pathways leading to (i). 5-perfluoroalkyl-1,3,4-oxadiazoles, through the ring contraction-ring expansion photoisomerization route favored by the presence of the base or (ii). 5-perfluoroalkyl-1,2,4-triazoles, through the intervention, as an internal nucleophile, of the exocyclic N-alkylamino moiety of the oxadiazole followed by the attack of the external nitrogen nucleophile and subsequ…

Concise asymmetric synthesis of Linezolid through catalyzed Henry reaction

2013

A new asymmetric synthesis of the antibiotic Linezolid was performed through a copper-catalyzed Henry reaction as the key step. The use of camphor-derived aminopyridine ligands helped to improve the yields of the chiral precursor and to obtain Linezolid in good overall yield and enantiomeric excess.

Chasing phthalates in tissues of marine turtles from the Mediterranean sea

2018

Tissues from thirteen specimens of marine turtles, one Dermochelys coriacea and twelve Caretta caretta, found dead along the Sicilian coasts in 2016 were analyzed for the presence of phthalates. Four phthalates (DEP, DBP, BBP, and DEHP) were found at different significant concentrations in liver and gonads, while only DBP was found in muscle tissues and at a fourfold lower concentration than other phthalates in Dermochelys coriacea. No traces of DEP were detected in C. caretta tissues where DOTP was also revealed. The presence of phthalates in fat tissue in specimens of C. caretta showed a major prevalence of the most lipophilic phthalates DEHP and DOTP. The total concentration of all analy…

Magnetic hybrid TiO 2 /Alg/FeNPs triads for the efficient removal of methylene blue from water

2018

A new adsorbent material with combined adsorption, photocatalytic, and magnetic properties has been suc- cessfully synthesized and tested for the efficient dye removal from methylene blue (MB) contaminated water. A facile non-thermal method was applied to synthesize a hybrid nanocomposite consisting of TiO2/calcium algi- nate (TiO/Alg) and magnetite (Fe3O4) nanoparticles (FeNPs). The potential of the adsorbent Alg as a barrier to prevent direct contact between the magnetic core and TiO2 was experimented by varying the synthesis condi- tions. The performance of four differently synthesized TiO2/Alg/FeNPs samples (TiO2/Alg/FeNPs-1, TiO2/Alg/ FeNPs-2, TiO2/Alg/FeNPs-3, and TiO2/Alg/FeNPs-4) wa…

Viologen-Alkene CT Complex: A Comparison Between Solution and Intrazeolite Behavior‡‡Financial support through the NSF and the Italian CNR is fully a…

2003

On the photoreaction of some 1,2,4-oxadiazoles in the presence of2,3-dimethyl-2-butene. Synthesis of N-imidoyl-aziridines

2007

Fhe photochemistry of some 3,5-disubstituted 1,2,4-oxadiazoles in the presence of 2,3-dimethyl-2-butene has been investigated. The irradiation in acetonitrile yielded differently substituted N-imidoyl-aziridines through an aziridination reaction involving an acyliminonitrene intermediate. Pyrolysis of N-imidoyl-aziridines produced the corresponding N-allylamidines through a ring opening process.

Controlled uptake of PFOA in adult specimens of Paracentrotus lividus and evaluation of gene expression in their gonads and embryos

2023

AbstractPerfluorooctanoic acid (PFOA) has been largely used in the manufacturing industry but a few years ago it turned out to be a dangerous pollutant which is now of concern for terrestrial and aquatic environments. Here, we investigated the bioaccumulation of PFOA in the sea urchin Paracentrotus lividus after exposure to different concentrations of the pollutant for 28 days. We observed rapid uptake of PFOA in the coelomic fluid collected weekly during the exposure period and high bioaccumulation in gonads at the end of the experiment. Interestingly, animals were also able to fast depurate when relocated to a clean environment. In addition, to assess the effect of PFOA on sea urchins’ ph…

Unexpectedly ambivalent O-2 role in the autocatalytic photooxidation of 2-methoxybenzyl alcohol in water

2015

An unusual autocatalytic photooxidation of 2-methoxybenzyl alcohol has been observed under UV irradiation in aqueous medium. The homogeneous oxidation is catalyzed by the corresponding aldehyde that is also the main oxidation product. The trend of alcohol disappearance rate matches the typical shape of an autocatalytic process, where a crucial and ambivalent role is played by the presence of molecular oxygen. Low oxygen concentrations give rise to a zero-order reaction since the beginning of irradiation, while higher amounts of oxygen reduce the alcohol oxidation rate until the aldehyde reaches a concentration high enough to speed up the alcohol's conversion. Experiments performed by varyin…

ChemInform Abstract: Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles.

2011

The hydrazinolysis of the oxadiazoles under optimized conditions allows a general synthesis of functionalized aminotriazole products which are of interest due to the biological activity of the heterocyclic system.

Synthesis and preliminary antibacterial evaluation of Linezolid-like 1,2,4-oxadiazole derivatives

2012

In the present study the synthesis of new Linezolid-like molecules has been achieved by substitution of the oxazolidinone central heterocyclic moiety with a 1,2,4-oxadiazole ring. Two series of 1,2,4-oxadiazoles, bearing different side-chains and containing a varying number of fluorine atoms, were synthesized and preliminarily tested for biological activity against some Gram-positive and Gram-negative bacteria using Linezolid and Ceftriaxone as reference drugs

Exploiting the CNC Side Chain in Heterocyclic Rearrangements: Synthesis of 4(5)-Acylamino-imidazoles

2010

A new variation on the Boulton-Katritzky reaction is reported, namely, involving use of a CNC side chain. A novel Montmorillonite-K10 catalyzed nonreductive transamination of a 3-benzoyl-1,2,4-oxadiazole afforded a 3-(alpha-aminobenzyl)-1,2,4-oxadiazole, which was condensed with benzaldehydes to afford the corresponding imines. In the presence of strong base, these imines underwent Boulton-Katritzky-type rearrangement to afford novel 4(5)-acylaminoimidazoles.

Dispositivo per estrarre e purificare analiti da una matrice

2013

Synthesis of new fluorinated low molecular weight (LMW) gelators

2011

Trasformazioni eterocicliche di 1,2,4-ossadiazoli fluorurati come substrati dielettrofili

2005

No effects of low-intensity endurance exercise on muscle necrosis in the diaphragm of mdx mice

2014

Duchenne muscular dystrophy (DMD) is characterized by progressive skeletal muscle weakness. We have previously shown that low-intensity endurance training prevented muscle damage (Frinchi et al, Int J Sports Med 2014). Since the effects of low-intensity endurance training on the the diaphragm in the mdx mouse model are unknown, in the same animals we investigated Cx39 protein levels (Western blotting) in homogenates of the diaphragm before and after training. Mdx and wild-type (WT) mice were randomly assigned to sedentary (mdx-S, n=17; WT-S, n=19) or trained (mdx-EX, n=14; WT-EX, n=16) groups. Low-intensity endurance training (running on a wheel) was done 5 days/week for 6 weeks at progress…

NOVEL ANTAGONISTS FOR AN Hsp60-BASED ANTICANCER CHAPERONOTHERAPY

2012

The Heat shock proteins (Hsps) are nowadays considered the most important cell chaperones, which result overexpressed in response to a number of cell stress stimuli.In tumor cells, when Hsp60 accumulates in the cytosol, without mitochondrial release, it exerts an anti-apoptotic effect, by inhibiting pro-caspase-3 (pC3) activation. In this context, our study aims to elucidate the structural details of the interaction between Hsp60 and pC3 and to design novel antagonists able to specifically block this interaction. The analysis of virtual screening results highlights the 4-(3-chloro-4-fluorophenylamino)- 6-[(1H-imidazol-4-yl-methyl)-3-carbonitrile-quinolines of type 1 and the N-{5-[1H-imidazo…

1,2,4-Ossadiazoli come “nitrogen-donor” nella sintesi foto-indotta di aziridine

2007

Synthesis of Isoxazoline Derivatives through Boulton–Katritzky Rearrangement of 1,2,4-Oxadiazoles

2013

The base-induced rearrangement of 1,2,4-oxadiazoles into isoxazoline derivatives is reported. This represents the first example of a three-atom side-chain rearrangement that involves a saturated CCO side chain at C-3 of the oxadiazole. Nonaromatic 3-amino-isoxazoline derivatives are obtained in good yields. Interestingly, this reaction occurs through the rearrangement of aromatic oxadiazoles to form less stable bonds than those that are broken.

Trasformazioni eterocicliche di 1,2,4-ossadiazoli fluorurati in reazioni ANRORC-like

2008

Characterization of isomeric organic cations by Esi/MS: 3-alkyl-5-(4-N-methylpyridinium)-1,2,4-oxadiazole cations, 5-alkyl-3-(4-N-methylpyridinium)-1…

2005

Anrorc rearrangements of fluorinated 1,2,4-oxadiazoles as an expedient route to fluorinated heterocycles

2006

Ionic liquid crystals based on 1,2,4-triazolium rings

2017

Ionic liquids crystals (ILCs) are a class of organic materials of great current interest. They show unique properties that can be exploited in many different fields, for example their use as solvents for extraction processes as well as electrolytes for batteries, fuel cells, dye-sensitised solar cells etc. [1-4] Moreover, in perfluorinated ILCs, the segregation of the perfluorocarbon chains promotes further self-organisation of the LC phases, adding to the materials further properties such as affinity for gases suitable for example in gas-storage. [5-7] A series of salts based on 5-(4-alkyloxyphenyl)-1,4-dimethyl-3-(perfluoroalkyl)-1,2,4-triazol-4-ium structures, differing in the length of …

Composti eterociclici fluorurati. Un approccio fotochimico alla sintesi di chinazolin-4-oni

2004

Designing fluorous domains. Pyridinium salts bearing a perfluoroalkylated oxadiazole moiety

2005

Composti eterociclici fluorurati. Sintesi di 2-ammino-pirimidine N-ossido e 1,2,4-triazine

2004

ASYMMETRIC SYNTHESIS OF LINEZOLID THROUGH CATALYZED HENRY REACTION

2013

Linezolid 1 is an antibacterial oxazolidinone approved by FDA in 2000 for the treatment of fastidious bacterial infections.1 The asymmetric synthesis of Linezolid-like molecules make use of the chiral pool approach, through the so-called Manninen reaction.2 This strategy requires the use of BuLi, low temperature and a long elaboration of the acetamide chain. Curiously, the only catalyzed approach toward the asymmetrical synthesis of Linezolid was just recently reported, and belongs to the use of proline-derived catalysts in aldol reactions as the key step.3 This procedure is quite interesting except for the low yield. Here we report a new synthesis of Linezolid, based on a Cu(II)-catalyzed …

Nuovi film elettrocromici

2008

Recent Advances in 1,2,4-Oxadiazole Chemistry

2005

POLYCHLORINATED BIPHENYLS ADSORPTION ONTO ALGINATE BEADS AND HYBRID ALGINATE MONTMORILLONITE BEADS: ISOTHERMAL AND KINETIC STUDIES

2013

Fluorinated heterocyclic compounds from ring-to-ring transformations of O-N bond containing azoles

2004

Chimica in fase gassosa di ioni radicali, cationi e anioni prodotti da ossime di 1,2,4-triazine fluorurate

2006

Ionic liquid crystals based on 3-perfluoalkyl-1,2,4-triazol-4-ium salts

2016

Liquid-crystalline ionic liquids (LC-ILs) are a class of organic materials that of great current interest: they are defined as organic salts that possess the properties of two interesting kinds of material – ionic liquids (ILs) and liquid crystals (LCs). LC-ILs combine many interesting features of ILs (e.g. low volatility and the ability to dissolve solutes with a range of polarities) as well as many attractive properties of LCs (e.g. their intrinsic order and anisotropy). This provides unique opportunities that can be exploited in many different fields, for example their use as solvents for extraction processes as well as electrolytes for batteries, fuel cells, and dye-sensitised solar cel…

A novel copper compound, CuNV110, induces apoptosis in tumor cells by dissociation of the Hsp60- pro-caspase 3 complex

2015

The biological activity of CuNV1110, a novel copper chemical compound, has been recently studied on cancer cells and it has been showed that it reduces the cell viability, in a dose and time dependent manner, and induces cell apoptosis. In this study we evaluated the possible mechanisms by which CuNV1110 induces cell apoptosis. In particular we looked at its effects on Hsp60 levels and caspase 3 activation. We used an in vitro model of a pulmonary mucoepidermoid carcinoma (NCI-H292 cells). We found that CuNV1110 reduces the cell viability and induces cell apoptosis in a dose/time dependent manner. Then, we found that Hsp60 levels decrease with the increasing concentrations of CuNV110; by co…

CuNV1110 induces dissociation of the Hsp60-pro-caspase 3 complex and activation of apoptosis in tumor cells

2014

Sintesi e valutazione biologica di 1,2,4-ossadiazoli analoghi del Linezolid

2011

Synthesis of isoxazoline derivatives by Boulton-Katritzky Rearrangements

2012

Sintesi one-pot di N-ossidi di 2-ammino-pirimidine fluorurate. Riarrangiamenti competitivi “four-atom side-chain” di 1,2,4-ossadiazoli

2005

Recent Advances in the Chemistry of 1,2,4-Oxadiazoles

2015

1,2,4-Oxadiazoles experienced an almost 80-year long period of scientific lethargy before they tickled the curiosity of chemists. The study of chemical and photochemical reactivity of 1,2,4-oxadiazoles opened the way to a series of applications in heterocyclic synthesis. Today, 1,2,4-oxadiazoles are known in medicinal chemistry for their use as bioisosters of esters and amides. Furthermore, fluorinated 1,2,4-oxadiazoles have been applied in materials science either by themselves or for the targeted modification of polymers and macromolecules. Overall, the synthesis of 1,2,4-oxadiazoles can be planned to fine-tune their properties for featured applications. Their versatility, either as start…

Fotodegradazione di esteri ftalici su pitture murali tramite irradiazioni uv

2014

Gli esteri ftalici (esteri dell’acido ftalico), rappresentano una particolare classe di inquinanti organici ubiquitari, resistenzi alla bio-degradazione, capaci da fungere da distruttori endocrini e dannosi a causa del loro effetto mutageno e cancerogeno. Molti composti di questa classe di sostanze per decenni, e probabilmente ancora oggi, sono stati utilizzati come ammorbidenti nelle pitture murali superficiali utilizzate nelle comuni abitazioni domestiche. Considerando quindi che oggigiorno, le attività di demolizione e ristrutturazione rapprsentano una cospiqua fetta di mercato delle attività edilizie, e che spesso i lavoratori impiegati in queste attività sono sogetti in maniera continu…

Nuovi Riarrangiamenti Boulton-Katritzky di derivati 1,2,4-ossadiazolici contenenti un atomo di carbonio nucleofilo in catena laterale

2009

Sintesi di nuovi bent-core LC fluorurati

2011

Effects of mild aerobic exercise training on the diaphragm in mdx mice

2016

Mild endurance exercise training positively affects limb skeletal muscle in the mdx mice model of Duchenne Muscular Dystrophy (DMD). However, few and controversial data are available on the effects of mild exercise training on the diaphragm of mdx mice. The diaphragm was examined in mdx and wild type mice either under sedentary conditions (mdx-SD, WT-SD) or during mild exercise training (mdx-EX, WT-EX). At baseline and after 30 and 45 days of training (5 d/wk for 6 weeks), diaphragm muscle morphology and Cx39 protein were assessed. In addition, tissue levels of the chaperonin Hsp60 were measured at the same time points in gastrocnemius, quadriceps and diaphragm in each experimental group. A…

Sintesi di sali di azolil-piridinio contenenti catene perfluoroalchiliche o alchiliche: alcune proprietà e potenziali applicazioni

2006

Identification and validation of novel molecules obtained by integrated computational and experimental approaches for the readthrough of PTCs in CF c…

2014

Cystic Fibrosis patients with nonsense-mutation in h-CFTR gene generally make virtually no CFTR protein and thus often have a more severe form of CF. Ataluren (PTC124) was suggested to induce read-through of premature but not normal termination codons. Despite the promising results there is not a general consensus on the mechanism of its action (protein stabilization or codon read-through) and its efficacy, the identification of new PTC124 analogues and the study of the mechanism of action may led to a new strategy for the development of a pharmacologic approach to the cure of CF.

Photochemical sample treatment: A greener approach for PCBs analysis in sediments

2012

Electrical installations and industrial outlets are the major source in environment of chlorinated organic compounds. These are distributed in several geographical areas through long-range atmospheric transport and deposition. Additionally, chlorinated organic compounds can be introduced in the food chain and reach the consumers in very high levels. Besides toxicological studies on PCBs, recent research is focusing on more sophisticated analytical methods for PCBs detection. Distribution and dispersion of PCBs mostly occur through air, water, soils, and sediments. The latter are complex matrices whose analysis often involves costly extraction and purification procedures. In particular, PCBs…

Experimental and DFT Studies on Competitive Heterocyclic Rearrangements. A Cascade Isoxazole-1,2,4-Oxadiazole-Oxazole Rearrangement

2009

The thermal rearrangements of 3-acylamino-5-methylisoxazoles 1 have been investigated under basic and neutral conditions and interpreted with the support of computational data. The density functional theory (DFT) study on the competitive routes available for the base-catalyzed thermal rearrangement of isoxazoles 1 showed that the Boulton-Katritzky (BK) rearrangement, producing the less stable 3-acetonyl- 1,2,4-oxadiazoles 5, is a much more favored process than either the migration-nucleophilic attack-cyclization (MNAC) or the ring contraction-ring expansion (RCRE). In turn, an increase in reaction temperature will promote the MNAC of oxadiazoles 5, producing the more stable 2-acylaminooxazo…

No effect of low-intensity endurance exercise on muscle necrosis in the diaphragm of mdx mice.

2014

Duchenne muscular dystrophy (DMD) is characterized by progressive skeletal muscle weakness. We have previously shown that low-intensity endurance training prevented muscle damage (Frinchi et al, Int J Sports Med 2014). Since the effects of low-intensity endurance training on the the diaphragm in the mdx mouse model are unknown, in the same animals we investigated C x39 protein levels (Western blotting) in homogenates of the diaphragm before and after training. Mdx and wild-type (WT) mice were randomly assigned to sedentary (mdx-S, n=17; WT-S, n=19) or trained (mdx-EX, n=14; WT-EX, n=16) groups. Low-intensity endurance training (running on a wheel) was done 5 days/week for 6 weeks at progres…

Polyfluoroalkyl viologen-based Ionic Liquid Crystals

2015

Studio dell’effetto dei sostituenti sul riarrangiamento fotoindotto di diaril-1,2,4-ossadiazoli in zeolite NaY

2008

Asymmetric synthesis and biological evaluation of 1,2,4-Oxadiazoles analogues of Linezolid

2014

Oxazolidinones are a class of antibacterial agents which displayed activity againist a variety of gram-positive pathogens and are highly potent against multidrug-resistant bacteria. Linezolid is the first oxazolidinone antibiotic approved for clinical use but linezolid resistance began to appear. 1,2,4 – Oxadiazoles are known bioactive heterocycles whose activity has been often associated to their bioisosterism with amide or ester functionalities [1]. As results of a research project on the molecular design of heterocycle – based antibacterials to contrast Multi-Drug Resistance (MDR) [2], we report the synthesis of 1,2,4 - Oxadiazole analogues of Linezolid. The synthesis has been achieved b…

Synthesis of trifluoromethylated 2-benzoyl- and 3-aminoimidazoles from ring rearrangement of 1,2,4-oxadiazole derivative

2008

Fluoroalkylated 2-ylamino-imidazoles have been synthesized by reaction of 3-amino-5-phenyl-1,2,4-oxadiazole with fluorinated b-dicarbonyl compounds and subsequent base-induced BoultoneKatritzky Rearrangement (BKR) of the isolated b-enaminocarbonyl intermediate. Alternatively, one-pot reactions performed in the presence of Montmorillonite K10 favoured the condensation at the 3-amino moiety of the oxadiazole and, in some cases, allowed the direct synthesis of 2-benzoylamino-imidazoles. Hydrolysis of 2-benzoylamino-imidazoles easily yielded fluorinated 2-amino-imidazoles targets.

Synthesis, Reactivity, Biological Activity and Applications of Fluorinated Oxadiazoles and Thiadiazoles

2014

A literature survey of the chemistry of fluorinated oxadiazoles and thiadiazoles is presented. The core part on synthetic procedures is given by type of heterocycle and includes recent developments up to the end of 2012. Reactivity is discussed when induced by the presence of the fluorinated moiety. Selected examples of bioactive compounds and applications are illustrated.

Sintesi di un nuovo sensore fluorescente selettivo per Hg2++ contenente ossadiazoli fluorurati

2009

AZIONE READTHROUGH DI DERIVATI DEL PTC124 SU SISTEMI MODELLO CELLULARI E IN CELLULE DI EPITELIO BRONCHIALE-FC IB3.1 (CFTR F508/W1282X )

2013

Obiettivi specifici: Le mutazioni nonsenso (mutazioni STOP), un difetto genetico frequente negli individui affetti da Fibrosi Cistica (CF), causano la sintesi di proteine CFTR tronche e non funzionanti che sono associate ad un fenotipo più severo della CF (McKone EF. et al., Chest 2006). L’obiettivo del nostro studio è stato quello di disegnare derivati dell’Ataluren (PTC124), una ‘small molecule’ a cui è stata attribuita attività readthrough, e valutarne l’attività su tre differenti sistemi modello sperimentali contenenti codoni di STOP prematuri (UGA, UAG, UAA). Materiali e metodi: Sono state sintetizzate 24 molecole derivate dal PTC124 e analizzate mediante tecniche spettroscopiche per v…

Synthesis and chemical characterization of CuII, NiII and ZnII complexes of 3,5-bis(20-pyridyl)-1,2,4-oxadiazole and 3-(20-pyridyl)5-(phenyl)-1,2,4-o…

2011

The synthesis and structural characterization of NiII, CuII and ZnII complexes of two chelating 1,2, 4-oxadiazole ligands, namely 3,5-bis(20-pyridyl)-1,2,4-oxadiazole (bipyOXA) and 3-(20-pyridyl)5- (phenyl)-1,2,4-oxadiazole (pyOXA), is here reported. The formed hexacoordinated metal complexes are [M(bipyOXA)2(H2O)2](ClO4)2 and [M(pyOXA)2(ClO4)2], respectively (M = Ni, Cu, Zn). X-ray crystallography, 1H and 13C NMR spectroscopy and C, N, H elemental analysis data concord in attributing them an octahedral coordination geometry. The two coordinated pyOXA ligands assume a trans coplanar disposition, while the two bipyOXA ligands are not. The latter result is a possible consequence of the format…

PTC124 DERIVATIVES AS A NOVEL APPROACH TO IMPROVE THE READTHROUGH OF PREMATURE AMBER AND OCHRE STOP CODONS

2013

Nucleotide changes within an exon may alter the trinucleotide normally encoding a particular amino acid, such that a new “stop” signal is transcribed into the mRNA open reading frame. This causes the ribosome to prematurely terminate its reading of the mRNA, leading to the lack of production of a normal full-length protein. Such premature termination codon (PTC) mutations occur in an estimated 10% to 15% of many genetically based disorders (1). Pathological nonsense mutations resulting in TAG (40.4%), TGA (38.5%), and TAA (21.1%) occur in different proportions to naturally occurring stop codons (2). Several genetic disorders are characterized by opal (TGA; Cystic fibrosis, Duchenne/Becker m…

Synthesis and biological evaluation of 1,4-oxadiazole analogues of Linezolid

2012

Sintesi di ossadiazoli fluorurati come nuovi Low molecular weight hydrogelators

2010

Sintesi di Low Molecular Weight Gelators (LMWG) Fluorurati

2011

Microreattori fluorurati. Studio della reazione "ene" con ossigeno singoletto in zeolite NAY modificata con cationi fluoroorganici

2006

Synthesis and characterization of a new set of protic ionic liquids

2012

Fluoroarylation of hydroxylated molecules with 5-pentafluorophenyl-1,2,4-oxadiazoles

2005

Synthesis and characterization of new azoles as building blocks for functional ionic systems

2015

Experimental and DFT studies on competitive heterocyclic rearrangements. part 2: A one-atom side-chain versus the classic three-atom side-chain (Boul…

2007

The experimental investigation of the base-catalyzed rearrangements of 3-acylamino-1,2,4-oxadiazoles evidenced a new reaction pathway which competes with the well-known ring-degenerate Boulton- Katritzky rearrangement (BKR). The new reaction consists of a one-atom side-chain rearrangement that is base-activated, occurs at a higher temperature than the BKR, and irreversibly leads to the corresponding 2-acylamino-1,3,4-oxadiazoles. An extensive DFT study is reported to elucidate the proposed reaction mechanism and to compare the three possible inherent routes: (i) the reversible three-atom side-chain ring-degenerate BKR, (ii) the ring contraction-ring expansion route (RCRE), and (iii) the one…

Nuovi film policromatici

2009

Fluorinated azole-azine systems as new Liquid-crystalline Ionic Liquids

2015

Fotochimica organica in zeolite: dalle fotoossidazioni ai riarrangiamenti eterociclici

2004

Sintesi di 1,2,4-ossadiazoli fluorurati analoghi del Linezolid come potenziali anti-batterici

2009

L'aumentata multidrug resistance tra i batteri patogeni Gram-positivi ha riacceso l'interesse verso la ricerca di nuove classi strutturali di antibiotici attivi nei confronti di batteri multiresistenti.1 Il Linezolid, appartenente alla classe degli ossazolidinoni, è il capostipite di una nuova generazione di anti-batterici di sintesi attivi contro patogeni Gram-positivi.2 La ricerca di nuovi analoghi del Linezolid risulta quanto mai attuale dato il recente riscontro di fenomeni di resistenza batterica a tale farmaco.3 In questo contesto, verranno presentati alcuni risultati preliminari relativi allo sviluppo di nuove metodologie di sintesi per l’ottenimento di composti eterociclici fluorura…

Applications of ring rearrangements involving a participating side chain for the synthesis of five-membered heterocycles

2014

Fluorinated heterocycles from 1,2,4-oxadiazole precursors. Synthesis of 3-amino-indazoles

2006

Novel ANRORC rearrangements of 1,2,4-oxadiazoles

2010

Synthesis of tetrasubstituted-4,4'-biimidazoles with perspective heavy-metal sensing ability

2012

CCDC 2077920: Experimental Crystal Structure Determination

2021

Related Article: Marco Saccone, Andrea Pace, Ivana Pibiri, Gabriella Cavallo, Pierangelo Metrangolo, Tullio Pilati, Giuseppe Resnati, Giancarlo Terraneo|2021|CrystEngComm|23|7324|doi:10.1039/D1CE01001H

CCDC 1848982: Experimental Crystal Structure Determination

2018

Related Article: Alessio Riccobono, Rachel R. Parker, Adrian C. Whitwood, John M. Slattery, Duncan W. Bruce, Ivana Pibiri, Andrea Pace|2018|Chem.Commun.|54|9965|doi:10.1039/C8CC04704A