Search results for "triazole"
showing 10 items of 347 documents
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.
Synthesis of ortho-fonctionnalized arylphosphines and their applications
2020
This thesis reports with the synthesis of ortho-functionnalized phosphines bearing phosphonium and 1,2,3-triazole moieties.The synthesis of phosphines-phosphoniums, using as key-step Phospha-Fries rearrangement and Appel reaction is described. Eight new phosphines- phosphoniums, bearing aryl, alkyl or ferrocenyl fragments on the phosphonium part, have been prepared with overall yields reaching 48%. These phosphines- phosphoniums have been used in the preparation of gold (I) complexes which have been characterized using spectroscopic methods and X ray diffraction. Both gold (I) complexes and phosphines-phosphoniums have been studied in biology and these compounds turned out to be cytotoxic i…
Effects of carboxyamidotriazole on in vitro models of imatinib-resistant chronic myeloid leukemia.
2008
Although imatinib mesylate (IM) has revolutionized the treatment of chronic myeloid leukemia (CML), some patients develop resistance with progression of leukemia. Alternative or additional targeting of signaling pathways deregulated in bcr-abl-driven CML cells may provide a feasible option for improving clinical response and overcoming resistance. In this study, we show that carboxyamidotriazole (CAI), an orally bioavailable calcium influx and signal transduction inhibitor, is equally effective in inhibiting the proliferation and bcr-abl dependent- and independent-signaling pathways in imatinib-resistant CML cells. CAI inhibits phosphorylation of cellular proteins including STAT5 and CrkL a…
Selinexor in Advanced, Metastatic Dedifferentiated Liposarcoma: A Multinational, Randomized, Double-Blind, Placebo-Controlled Trial
2022
PURPOSE Antitumor activity in preclinical models and a phase I study of patients with dedifferentiated liposarcoma (DD-LPS) was observed with selinexor. We evaluated the clinical benefit of selinexor in patients with previously treated DD-LPS whose sarcoma progressed on approved agents. METHODS SEAL was a phase II-III, multicenter, randomized, double-blind, placebo-controlled study. Patients age 12 years or older with advanced DD-LPS who had received two-five lines of therapy were randomly assigned (2:1) to selinexor (60 mg) or placebo twice weekly in 6-week cycles (crossover permitted). The primary end point was progression-free survival (PFS). Patients who received at least one dose of st…
A recent portrait of bioactive triazoles
2010
Scientists have extensively explored new synthetic routes in order to obtain 1,2,3- and 1,2,4-triazoles as they represent a very interesting class of compounds due to their wide range of biological activities such as antitumor, antiinflammatory, analgesic, antifungal, antibacterial, antiviral, etc. This mini review reports the synthesis and the biological activities of compounds containing a triazole moiety published since 2007. No attempt is made to provide a comprehensive literature overview, our aim is to highlight some more recent examples of synthetic biological active compounds. In particular, we focus on the applications of “click reactions” that allow the regioselective synthesis of…
On the rearrangement of some Z-arylhydrazones of 3-benzoyl-5-phenylisoxazoles into 2-aryl-4-phenacyl-2H-1,2,3-triazoles: a kinetic study of the subst…
2015
Abstract The rearrangement of eight new Z -arylhydrazones of 3-benzoyl-5-phenylisoxazoles ( 3d – k ) into the relevant 2-aryl-4-phenacyl-2 H -1,2,3-triazoles ( 4d – k ) in dioxane/water solution at different proton concentrations has been quantitatively studied in a wide temperature range (293–333 K). The data collected together with some our previous ones on compounds 3a – c have allowed a deep study of the substituent effects on the course of the rearrangement, thus increasing our knowledge on the Boulton–Katritzky reactions in isoxazole derivatives and on the temperature effects on free energy relationships.
An unexpected Dimroth rearrangement leading to annelated thieno[3,2-d][1,2,3]triazolo[1,5-a]pyrimidines with potent antitumor activity.
2013
An unusual Dimroth rearrangement occurring in the reaction leading to annelated thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidine core allowed the isolation of the linear isomer thieno[3,2-d][1,2,3]triazolo[1,5-a]pyrimidine. By decorating the linear isomer with the same chains that improved the biological activity of the angular isomers, new annelated thieno[3,2-d][1,2,3]triazolo[1,5-a]pyrimidines were designed and synthesized. They were selected by the Developmental Therapeutics Program (DTP) of the National Cancer Institute (NCI) for the anticancer screening against a panel of 60 human tumor cell lines. The biological results showed that the new derivatives exhibited strong antiproliferative …
New annelated thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines, with potent anticancer activity, designed through VLAK protocol
2012
Drug design was performed through the Virtual Lock-and-Key (VLAK) protocol. This in silico approach allowed to select new annelated thienotriazolopyrimidine derivatives, potentially antitumor drugs. Starting from benzothieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidine and Pyrido[3',2':4,5]thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidine core structures, new derivatives of these nuclei were designed and synthesized. Three of them were selected by the Development Therapeutical Program (DTP) of the National Cancer Institute (NCI) for the anticancer screening against a panel of 60 human tumor cell lines. The biological results showed that the new derivatives exhibited an excellent antiproliferative act…
Copper(II)-dipicolinate-mediated clickable azide–alkyne cycloaddition in water as solvent
2018
Copper(II)-dipicolinate complex [CuIIL(H2O)2] (1) (H2L = dipicolinic acid (H2dipic)) was synthesized via oxidation of copper(I) iodide and pyridine-2,6-dicarboxylic acid in water and acetonitrile in the presence of glycine. Complex 1 was characterized by FT-IR and elemental analysis and its structure confirmed by single crystal X-ray analysis. This complex is an efficient precatalyst that mediates azide-alkyne cycloaddition reactions in water at room temperature either in the absence or presence of a reducing agent. Compound 1-mediated azide-alkyne cycloaddition affords alkyl/aryl substituted 1,2,3-triazole heterocycles in a regioselective manner and excellent yields under very mild reactio…
Directional Shuttling of a Stimuli-Responsive Cone-Like Macrocycle on a Single-State Symmetric Dumbbell Axle
2018
Rotaxane-based molecular shuttles are often operated using low-symmetry axles and changing the states of the binding stations. A molecular shuttle capable of directional shuttling of an acid-responsive cone-like macrocycle on a single-state symmetric dumbbell axle is now presented. The axle contains three binding stations: one symmetric di(quaternary ammonium) station and two nonsymmetric phenyl triazole stations arranged in opposite orientations. Upon addition of an acid, the protonated macrocycle shuttles from the di(quaternary ammonium) station to the phenyl triazole binding station closer to its butyl groups. This directional shuttling presumably originates from charge repulsion and an …