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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Journal ArticleDOI
One-pot chemoenzymatic synthesis of chiral disubstituted 1,2,3-triazoles in aqueous media
TL;DR: In this article, a one-pot, two-step procedure combining 1,3-dipolar cycloaddition and an enantioselective reduction mediated by Daucus carota (carrot root) is described.
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Synthesis of 5-organostibano-1H-1,2,3-triazoles by Cu-catalyzed azide-alkyne cycloaddition and their application in the acyl-induced deantimonation for the preparation of fully substituted 5-acyl-1,2,3-triazoles
Mizuki Yamada,Mio Matsumura,Yuki Murata,Masatoshi Kawahata,Kohki Saito,Naoki Kakusawa,Kentaro Yamaguchi,Shuji Yasuike +7 more
TL;DR: In this article, the reaction of various ethynylstibanes with benzylazide in the presence of CuBr under aerobic conditions led to the formation of trisubstituted 5-organostibano-1H-1,2,3-triazoles.
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Click chemistry-based synthesis and cytotoxic activity evaluation of 4α-triazole acetate podophyllotoxin derivatives.
TL;DR: In vitro cytotoxic activity evaluation showed that most of the derivatives exhibited potent inhibitory activities against the tested cancer cell lines with low nanomolar IC50 values, and further studies demonstrated that compound 31 exhibited broad‐spectrum cytot toxic activities, effectively overcame drug‐resistance, and showed relatively weak cytotoxicity on non‐cancer cells.
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Supramolecular Ensemble of Perylene Bisimide Derivative and Cu2O-Ag Nanoparticles: Nano/“Dip Strip” Catalytic System for One-Pot, Three-Component Click Reaction at Room Temperature
TL;DR: A supramolecular ensemble of Cu2O-Ag nanoparticles (NPs) and aggregates of perylene bisimide (PBI) derivative has been developed in mixed aqueous media.
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Transformation of Alkynes into α- or β-Difluorinated Alkyl Azides by an Efficient One-Pot Two-Step Procedure.
TL;DR: An unprecedented 1,2-azide migratory hydroazidation and subsequent gem-difluorination of alkynes accessing β-dIFluorinated alkyl azides is reported, and the azide group is sustained up to the final product.
References
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A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
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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.
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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.
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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.
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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.