Search results for "cyclobutane"
showing 10 items of 35 documents
CCDC 2051973: Experimental Crystal Structure Determination
2021
Related Article: Jan Sietmann, Mike Ong, Christian Mück-Lichtenfeld, Constantin G. Daniliuc, Johannes M. Wiest|2021|Angew.Chem.,Int.Ed.|60|9719|doi:10.1002/anie.202100642
A novel moniliformin derivative as pan-inhibitor of histone deacetylases triggering apoptosis of leukemia cells
2021
New and potent agents that evade multidrug resistance (MDR) and inhibit epigenetic modifications are of great interest in cancer drug development. Here, we describe that a moniliformin derivative (IUPAC name: 3-(naphthalen-2-ylsulfanyl)-4-{[(2Z)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]methyl}cyclobut-3-ene-1,2-dione; code: MCC1381) bypasses P-gp-mediated MDR. Using transcriptomics, we identified a large number of genes significantly regulated in response to MCC1381, which affected the cell cycle and disturbed cellular death and survival. The potential targets of MCC1381 might be histone deacetylases (HDACs) as predicted by SwissTargetPrediction. In silico studies confirmed that MCC13…
Chromogenic Detection of Nerve Agent Mimics by Mass Transport Control at the Surface of Bifunctionalized Silica Nanoparticles
2010
Chemical warfare (CW) agents are toxic chemicals that have been used in several terrorist attacks in recent years. Among CW species, nerve agents are probably the most dangerous; their high toxicity and facile synthesis underscores the need to detect these lethal compounds with quick, reliable procedures. Analytical methods based on enzymatic assays and physical measurements have generally been used to detect these hazards. However, these protocols usually have limitations such as low selectivity, poor portability, and a certain level of complexity. In recent years, several chromogenic and fluorogenic sensors, and reagents for the detection of nerve agents have been described. For instance,…
Gold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes
2014
α,β-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.
Counterintuitive Mechanisms of the Addition of Hydrogen and Simple Olefins to Heavy Group 13 Alkene Analogues
2013
The mechanism of the reaction of olefins and hydrogen with dimetallenes ArMMAr (Ar = aromatic group; M = Al or Ga) was studied by density functional theory calculations and experimental methods. The digallenes, for which the most experimental data are available, are extensively dissociated to gallanediyl monomers, :GaAr, in hydrocarbon solution, but the calculations and experimental data showed also that they react with simple olefins, such as ethylene, as intact ArGaGaAr dimers via stepwise [2 + 2 + 2] cycloadditions due to their considerably lower activation barriers vis-à-vis the gallanediyl monomers, :GaAr. This pathway was preferred over the [2 + 2] cycloaddition of olefin to monomeric…
Squaramide-based reagent for selective chromogenic sensing of Cu(II) through a zwitterion radical.
2010
A minimalist squaramide-based chemodosimeter for Cu(2+) is described. Upon selective chelation to 2, Cu(2+) induces the formation of a highly colored zwitterionic radical, which is kinetically stable for hours. The presence of a radical is confirmed by EPR and ESI-MS. It is then possible to use reagent 2 for visual and selective sensing of Cu(2+) at neutral pH.
Squaric Acid Mediated Synthesis and Biological Activity of a Library of Linear and Hyperbranched Poly(Glycerol)-Protein Conjugates
2012
Polymer-protein conjugates generated from side chain functional synthetic polymers are attractive because they can be easily further modified with, for example, labeling groups or targeting ligands. The residue specific modification of proteins with side chain functional synthetic polymers using the traditional coupling strategies may be compromised due to the nonorthogonality of the side-chain and chain-end functional groups of the synthetic polymer, which may lead to side reactions. This study explores the feasibility of the squaric acid diethyl ester mediated coupling as an amine selective, hydroxyl tolerant, and hydrolysis insensitive route for the preparation of side-chain functional, …
Intra- and extra-cellular DNA damage by harmine and 9-methyl-harmine
2014
It is known that b-carbolines are able to produce photosensitized damage in cell-free DNA, but there is little information on their effects on cellular DNA. Therefore, we have analyzed the DNA damage produced by harmine and 9-methyl-harmine under UVA irradiation in V79 cells, together with the associated generation of micronuclei and photocytotoxicity. The results indicate that the most frequent photoproducts generated in the cellular DNA are modified purines such as 8-oxo-7,8-dihydroguanine. Only relatively few single-strand breaks were observed. CPDs were absent, although they were generated in cell-free DNA irradiated under the same conditions. The overall extent of DNA damage in the cel…
Strukturuntersuchungen von polyamiden aus cyclischen dicarbonsäuren und piperazin durch direkten abbau im massenspektrometer
1977
Polyamide aus 1,2-Cyclobutan-, 1,2-Cyclopentan- und 1,2-Cyclohexandicarbonsaure und Piperazin wurden direkt in der Ionenquelle eines Massenspektrometers pyrolysiert. Die hohe Empfindlichkeit der massenspektrometrischen Methode erlaubt, bei Abbauraten von ca. 1%/min zu pyrolysieren und dadurch selektive thermische Abbaumechanismen neben den Fragmentierungsreaktionen nachzuweisen. Durch thermischen Abbau werden dabei Oligomere mit Piperazinendgruppen sowie gesattigte und ungesattigte Cyclobutan-, -pentan- und -hexanendgruppen gebildet. Polyamides of 1,2-cyclobutane-, 1,2-cyclopentane- and 1,2-cyclohexane-dicarboxylic acid and piperazine were pyrolyzed directly in the ion source of a mass spec…
Squaric acid mediated chemoselective PEGylation of proteins: reactivity of single-step-activated α-amino poly(ethylene glycol)s.
2012
The covalent attachment of poly(ethylene glycol) (PEG) to therapeutically active proteins (PEGylation) has become an important method to deal with the pharmacological difficulties of these polypeptides, such as short body-residence times and immunogenicity. However, the derivatives of PEG used for PEGylation lack further functional groups that would allow the addition of targeting or labeling moieties. Squaric acid diethyl ester was used for the chemoselective single-step activation of poly(ethylene glycol)s into the respective ester amides. The resultant selective protein-reactive poly(ethylene glycol)s were investigated with respect to their selectivity towards amino acid residues in bovi…