Click Chemistry: 1,2,3‐Triazoles as Pharmacophores
TLDR
The present review will focus mainly on the recent literature for applications of this reaction in the field of medicinal chemistry, in particular on use of the 1,2,3-triazole moiety as pharmacophore.Abstract:
The copper(I)-catalyzed 1,2,3-triazole-forming reaction between azides and terminal alkynes has become the gold standard of 'click chemistry' due to its reliability, specificity, and biocompatibility. Applications of click chemistry are increasingly found in all aspects of drug discovery; they range from lead finding through combinatorial chemistry and target-templated in vitro chemistry, to proteomics and DNA research by using bioconjugation reactions. The triazole products are more than just passive linkers; they readily associate with biological targets, through hydrogen-bonding and dipole interactions. The present review will focus mainly on the recent literature for applications of this reaction in the field of medicinal chemistry, in particular on use of the 1,2,3-triazole moiety as pharmacophore.read more
Citations
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Medicinal attributes of 1,2,3-triazoles: Current developments
TL;DR: The present work aims to summarize the current approaches adopted for the synthesis of the 1,2,3-triazole and medicinal significance of these architectures as a lead structure for the discovery of drug molecules such as COX-1/COX-2 inhibitors, HIV protease inhibitors, CB1 cannabinoid receptor antagonist and much more which are in the pipeline of clinical trials.
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Copper-catalysed azide-alkyne cycloadditions (CuAAC): an update.
TL;DR: The recent results described in the literature since 2010 are reviewed, classified according to the nature of the catalyst precursor: copper(I) or copper(II) salts or complexes, metallic or nano-particulated copper and several solid-supported copper systems.
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Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications.
TL;DR: The ruthenium-catalyzed azide alkyne cycloaddition affords 1,5-disubstituted 1,2,3-triazoles in one step and complements the more established copper-Catalyzed reaction providing the 1,4-isomer.
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Robust Ruthenium(II)-Catalyzed C–H Arylations: Carboxylate Assistance for the Efficient Synthesis of Angiotensin-II-Receptor Blockers
TL;DR: Ruthenium(II) complexes have emerged as effective catalysts for C-H arylations of tetrazolyl-substituted arenes by chelation assistance.
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Metal-Catalyzed Azide-Alkyne “Click” Reactions: Mechanistic Overview and Recent Trends
TL;DR: In this paper, a review of the mechanistic aspects and recent trends of metal-catalyzed azide-alkyne cycloaddition (MAAC) reactions with catalysts based on various metals (Cu, Ru, Ag, Au, Ir, Ni, Zn, Ln), although Cu (I) catalysts are still the most used ones.
References
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Synthesis of novel 3-(1-(1-substituted piperidin-4-yl)-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazol-5(4H)-one as antifungal agents.
TL;DR: A novel series of 1, 2,3 triazole compounds possessing 1,2,4 oxadiazole ring were efficiently synthesized and evaluated for their in vitro antifungal activities using standard cup plate method.
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Synthesis and evaluation of new difluoromethyl azoles as antileishmanial agents
Sabrina Baptista Ferreira,Marilia S. Costa,Nubia Boechat,Rômulo José Soares Bezerra,Marcelo Genestra,Marilene M. Canto-Cavalheiro,Warner B. Kover,Vitor F. Ferreira +7 more
TL;DR: The results show that the introduction of the difluoromethylene moieties has turned the inactive carbaldehydes into active antileishmanial compounds.
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2-triazole-substituted adenosines: a new class of selective A3 adenosine receptor agonists, partial agonists, and antagonists
Liesbet Cosyn,Krishnan K. Palaniappan,Soo-Kyung Kim,Heng T. Duong,Zhan-Guo Gao,Kenneth A. Jacobson,Serge Van Calenbergh +6 more
TL;DR: N(6)-substituted 2-(1,2,3-triazolyl)adenosine analogues constitute a novel class of highly potent and selective nucleoside-based A(3)AR antagonists, partial agonists, and agonists.
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Synthesis of stable and selective inhibitors of human galectins-1 and -3.
Denis Giguère,Marc-André Bonin,Philipe Cloutier,Ramesh Patnam,Christian St-Pierre,Sachiko Sato,René Roy +6 more
TL;DR: Transition metal-catalyzed cross-coupling reactions were used to create carbon-carbon bond formation to create novel 2-aminothiazoles which reacted with a panel of acylating and sulfonylating reagents and best monovalent inhibitor among the tested series was (E)-methyl 2-phenyl-4-(beta-D-galactopyranosyl)-but-2-enoate 15.
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Synergistic Effect of Zanamivir—Porphyrin Conjugates on Inhibition of Neuraminidase and Inactivation of Influenza Virus
Wen-Hsien Wen,Mengi Lin,Ching-Yao Su,Ching-Yao Su,Shi-Yun Wang,Yih-Shyun E. Cheng,Jim-Min Fang,Jim-Min Fang,Chi-Huey Wong,Chi-Huey Wong +9 more
TL;DR: New anti-influenza agents of tetravalent zanamivir on a porphyrin scaffold were synthesized, which are 10 to 100 times more potent in inhibiting influenza replications even though they are somewhat less potent in neuraminidase inhibition than the monomeric zanAMivir.