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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Synthesis of 2-triazolyl-imidazo[1,2-a]pyridine through a one-pot three-component reaction using a nano copper oxide assisted click-catalyst
TL;DR: In this paper, the synthesis of 2-triazolyl imidazo[1,2-a]pyridine (8a-o) was accomplished through three component A3 coupling followed by 5-exo dig cyclisation by employing 1-alkyl-1, 2, 3-triaxole-4-carbaldehyde, amidine and terminal alkynes using 5 mol% nanocopper oxide together with 10 mol% sodium ascorbate as a click-catalyst in ethanol at 70 °C.
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Synthesis of copper catalysts for click chemistry from distillery wastewater using magnetically recoverable bionanoparticles
Richard L. Kimber,Fabio Parmeggiani,Nimisha Joshi,Alexander M. Rakowski,Sarah J. Haigh,Nicholas J. Turner,Jonathan R. Lloyd +6 more
TL;DR: In this article, copper recovered from a whisky distillery waste stream is shown to be an effective catalyst for a range of azide-alkyne "click" reactions, and a Biogenic Nanomagnetite (BNM) was used to rapidly recover and subsequently support the Cu catalyst.
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Binuclear Cu(I) complex of (N′1E,N′2E)-N′1,N′2-bis(phenyl(pyridin-2-yl)methylene)oxalohydrazide: Synthesis, crystal structure and catalytic activity for the synthesis of 1,2,3-triazoles
TL;DR: In this paper, a binuclear 5-coordinate distorted trigonal bipyramidal Cu(I) complex with oxalohydrazide (H2bpoh) was synthesized, and characterized by spectroscopic and single crystal X-ray diffraction techniques.
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From 1-Sulfonyl-4-aryl-1,2,3-triazoles to 1-Allenyl-5-aryl-1,2,3-triazoles
TL;DR: An efficient and highly regioselective synthesis of 1-allenyl-5-aryl-1,2,3-triazoles from 1-sulfonyl-4-aryl
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Design, Synthesis, and Anti-Bacterial Evaluation of Triazolyl-Pterostilbene Derivatives.
TL;DR: The design and synthesis of a series of triazolylpterostilbene derivatives confirmed that the design could successfully increase the inhibitory activity and specificity against MRSA and could be used as a candidate for anti-bacterial agents.
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.