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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β-Cyclodextrin-catalyzed three-component synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles from propynals, trimethylsilyl azide and malononitrile in water
Alevtina S. Medvedeva,Maria M. Demina,Tran D. Vu,Mikhail V. Andreev,Nina S. Shaglaeva,Lyudmila I. Larina +5 more
TL;DR: An efficient green method for the selective synthesis of new 4,5-disubstituted 1H-1,2,3-triazoloalkylidenes via the β-cyclodextrin-catalyzed three-component reaction between substituted propynals, trimethylsilyl azide and malononitrile in water at room temperature has been developed.
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Fluoroalkyl N -sulfonyl hydrazones: An efficient reagent for the synthesis of fluoroalkylated compounds
Paramasivam Sivaguru,Xihe Bi +1 more
TL;DR: A comprehensive review of the literature on fluoroalkyl N -sulfonyl hydrazones can be found in this article, where the classification of different reactivity profiles and the efficiencies of similar types of reactions or substrates with fluoro-alkyl diazo compounds are compared.
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Green synthesis of 1,2,3-triazoles via Cu2O NPs on hydrogen trititanate nanotubes promoted 1,3-dipolar cycloadditions
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A simple route towards the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from primary amines and 1,3-dicarbonyl compounds under metal-free conditions
TL;DR: An acetic acid-promoted approach that enables the synthesis of 1,4,5-trisubstituted 1,2,3-triazole derivatives has been achieved.
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Nucleoside dimers analogues with a 1,2,3-triazole linkage: conjugation of floxuridine and thymidine provides novel tools for cancer treatment. Part II.
TL;DR: Two groups of nucleoside dimers analogs possessing a different arrangement of the 1,4-disubstituted 1,2,3-triazole linkage show moderate anticancer activity, with cytostatic studies in three different cancer cell lines.
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.