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
A Stereoselective, Base‐free, Palladium‐Catalyzed Heck Coupling Between 3‐halo‐1,4‐Naphthoquinones and Vinyl‐1 H ‐1,2,3‐Triazoles
Dora C. S. Costa,Luana da S. M. Forezi,Milena D. Lessa,Maicon Delarmelina,Beatriz Matuck,Maria C.R. Freitas,Vitor F. Ferreira,Jackson A. L. de C. Resende,José Walkimar de M. Carneiro,Fernando de C. da Silva +9 more
TL;DR: In this article , a Heck coupling between 1,4naphthoquinone and 1H-1,2,3-triazole derivatives was reported for the first time.
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Interrupted Click Reaction with CuCF2CF3 Reagent: Synthesis of 5-Pentafluoroethyl 1,2,3-Triazoles.
Xinkan Yang,Gavin Chit Tsui +1 more
TL;DR: In this article , a three-component interrupted click reaction was used to synthesize novel 5-pentafluoroethyl 1,2,3-triazoles in one step from readily available terminal alkynes and azides.
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Direct CH (Het)arylation of 1,2‐Heteroazoles, Heterodiazoles, and Triazoles
TL;DR: In this article , a review of the recent developments in the direct CH (het)arylation of 1,2-heteroazoles, heterodiazoles, and triazoles is presented.
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Synthesis of 4-(1,2,3-triazol-1-yl)-L-phenylalanines
Nitin Bagra,Rahul Jain +1 more
TL;DR: In this article , a new structural class of phenylalanine derivatives is described, which are derived via copper-ligand catalysis with sodium azide under microwave irradiation followed by regioselective copper-catalyzed azide-terminal alkyne cycloaddition.
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Synthesis and Evaluation of (1,4-Disubstituted)-1,2,3-triazoles as Estrogen Receptor Beta Agonists
TL;DR: 1-(4-hydroxyphenyl)-α-phenyl-1,2,3-triazole-4-ethanol (21) was found to be the most potent analog and exhibited a general qualitative trend consistent with the measured EC50 values.
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.