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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Five-membered N-Heterocycles Synthesis Catalyzed by Nano-silica Supported Copper(II)–2-imino-1,2-diphenylethan-1-ol Complex
TL;DR: In this article, a new amino functionalized nano silica was synthesized using 2-hydroxy-1,2-diphenylethanthan-1-one.
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One-pot synthesis of 3-triazolyl-2-iminochromenes via a catalytic three component cascade reaction.
TL;DR: A variety of 3-triazolyl-2-iminochromenes were synthesized in a one-pot, catalytic, three component condensation, inducing an aldol-cyclization-dehydration sequence in the presence of a salicylaldehyde.
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Denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids
TL;DR: Palladium-catalyzed denitrogenative Suzuki and carbonylative Suzuki reactions of benzotriazoles with boronic acids have been achieved through the in situ generation of ortho-amino-arenediazonium species.
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1, 2, 3-Triazoles: scaffold with medicinal significance
TL;DR: This review throws light on the detailed synthetic approaches which have been used for the synthesis of Triazoles since the early development in the area of triazole chemistry and may help the medicinal chemists to develop new leads possessing 1,2,3-triazoles nucleus with higher efficacy.
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Coupling biocatalysis and click chemistry: one-pot two-step convergent synthesis of enantioenriched 1,2,3-triazole-derived diols
TL;DR: A fully convergent one-pot two-step synthesis of different chiral 1,2,3-triazole-derived diols in high yields and excellent enantio- and diastereoselectivities has been achieved by combining a single alcohol dehydrogenase (ADH) with a Cu-catalysed 'click' reaction.
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.