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
More filters
Journal ArticleDOI
CuO-Nanoparticles Catalyzed Synthesis of 1,4-Disubstituted-1,2,3-Triazoles from Bromoalkenes
TL;DR: A novel and efficient protocol involving commercially available CuO nanoparticles (CNP) as catalyst has been developed for the synthesis of 1,2,3-triazoles with good to excellent yields.
Journal ArticleDOI
Evaluation of bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)2) as catalyst for the synthesis of 1-glycopyranosyl-4-substituted-1,2,3-triazoles
TL;DR: This catalyst proved superior to the CuSO(4)/L-ascorbic acid system even with sterically hindered and less reactive glycosyl azides.
Journal ArticleDOI
Study of the Cytotoxic and Bactericidal Effects of Sila-substituted Thioalkyne and Mercapto-thione Compounds based on 1,2,3-Triazole Scaffold.
TL;DR: The results of the time‐kill assay suggested that the compound of 3e completely inhibited the growth of both gram‐negative bacteria, A. baumannii, and gram‐positive bacteria, S. aureus, which could be applicable for developing dual‐targeting anticancer/antibacterial therapeutics.
Journal ArticleDOI
A general method of Suzuki–Miyaura cross-coupling of 4- and 5-halo-1,2,3-triazoles in water
Pavel S. Gribanov,Pavel S. Gribanov,Gleb A. Chesnokov,Maxim A. Topchiy,Maxim A. Topchiy,Andrey F. Asachenko,Andrey F. Asachenko,Mikhail S. Nechaev,Mikhail S. Nechaev +8 more
TL;DR: A general method of the synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by Suzuki-Miyaura cross-coupling from 4- and 5-halo-1-2, 3-Triazoles is reported.
Journal ArticleDOI
E- or Z-Selective synthesis of 4-fluorovinyl-1,2,3-triazoles with fluorinated second-generation Julia–Kocienski reagents
TL;DR: In situ desilylation and Cu-catalyzed ligation reaction of TMS-protected α-fluoropropargyl benzothiazole sulfone with aryl, alkyl, and metallocenyl azides furnished second-generation Julia-Kocienski reagents in good to excellent yields.
References
More filters
Journal ArticleDOI
A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
Journal ArticleDOI
Click Chemistry: Diverse Chemical Function from a Few Good Reactions.
TL;DR: In this paper, a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links (C-X-C), an approach called click chemistry is defined, enabled, and constrained by a handful of nearly perfect "springloaded" reactions.
Journal ArticleDOI
Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.
TL;DR: A novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported, and the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1, 3-dipoles entering the reaction.
Journal ArticleDOI
Cu-catalyzed azide-alkyne cycloaddition.
TL;DR: The basis for the unique properties and rate enhancement for triazole formation under Cu(1) catalysis should be found in the high ∆G of the reaction in combination with the low character of polarity of the dipole of the noncatalyzed thermal reaction, which leads to a considerable activation barrier.
Journal ArticleDOI
The growing impact of click chemistry on drug discovery.
TL;DR: The copper-(I)-catalyzed 1,2,3-triazole formation from azides and terminal acetylenes is a particularly powerful linking reaction, due to its high degree of dependability, complete specificity, and the bio-compatibility of the reactants.