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
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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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Journal ArticleDOI
Rotaxanes and Catenanes by Click Chemistry
Ognjen Š. Miljanić,William R. Dichtel,William R. Dichtel,Ivan Aprahamian,Rosemary D. Rohde,Heather D. Agnew,James R. Heath,J. Fraser Stoddart +7 more
TL;DR: The crystal structure of a donor/acceptor catenane formed using the CuAAC reaction indicates that any secondary [p ··· p] interactions between the 1,2,3-triazole ring and the bipyridinium p-acceptor are certainly not destabilizing.
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Click chemistry to probe Hsp90: Synthesis and evaluation of a series of triazole-containing novobiocin analogues.
TL;DR: A series of triazole-containing novobiocin analogues has been designed, synthesized and their inhibitory activity determined, supporting a common mode of Hsp90 inhibition for both structural classes.
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Synthesis, antiplatelet and in silico evaluations of novel N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides
Alessandro K. Jordão,Vitor F. Ferreira,Emerson Silva Lima,Maria Cecília B. V. de Souza,Eduardo C.L. Carlos,Helena Carla Castro,Reinaldo B Geraldo,C. R. Rodrigues,Maria C.B. Almeida,Anna C. Cunha +9 more
TL;DR: Among NAH derivatives 2a-j, the compounds 2a, 2c, 2e, 2g and 2h were the most promising molecules with significant antiplatelet activity.
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Synthesis of 1,2,3-triazolo-carbanucleoside analogues of ribavirin targeting an HCV in replicon.
Yoshio Saito,Vanessa Escuret,David Durantel,Fabien Zoulim,Raymond F. Schinazi,Luigi A. Agrofoglio +5 more
TL;DR: The synthesis of carbocyclic and phosphonocarbocyClic analogues of ribavirin, an anti-HCV inhibitor, are described and displayed a moderate IC(50) against HIV-1 and 37 microM, respectively.
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Quick Assembly of 1,4-Diphenyltriazoles as Probes Targeting β-Amyloid Aggregates in Alzheimer's Disease
TL;DR: Preliminary results strongly suggest that use of click chemistry, which led to a 1,4-diphenyltriazole-based core, is a highly convenient and flexible approach for assembling novel imaging agents for targeting Abeta aggregates in senile plaques in the living human brain.