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
Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives
Priscila López-Rojas,Monika Janeczko,Konrad Kubiński,Ángel Amesty,Maciej Masłyk,Ana Estévez-Braun +5 more
TL;DR: Based on their minimal inhibitory concentrations (MICs) against selected microorganisms, six out of twenty-six compounds showed significant antibacterial activity towards Enterococcus faecalis and the synthesized triazoles show relatively low toxicity against human erythrocytes.
Journal ArticleDOI
Recent Advances in Multicomponent Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles
TL;DR: The recent progress regarding synthetic approaches towards differently substituted types of 1,2,3-triazoles via MCRs and the relevant mechanistic investigations is summarized in this review.
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Ultrasound promoted one pot synthesis of novel fluorescent triazolyl spirocyclic oxindoles using DBU based task specific ionic liquids and their antimicrobial activity.
TL;DR: An efficient one pot four-component domino reaction of 1-(prop-2-ynyl)indoline-2,3-dione, cyclic 1, 3-diketones, malononitrile and various aryl azides in DBU based ionic liquids under ultrasonic irradiation for the construction of heterocycles is described.
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Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents.
Fei-hu Cui,Fei-hu Cui,Jing Chen,Zu-Yu Mo,Shi-Xia Su,Yan-Yan Chen,Xian-Li Ma,Hai-Tao Tang,Heng-Shan Wang,Ying-Ming Pan,Xu Yanli,Xu Yanli +11 more
TL;DR: The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred and the resulting multisubstituted 5-seleno-1,2,3-triazoles showed potent cancer cell-growth inhibition activities.
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An enolate-mediated organocatalytic azide-ketone [3+2]-cycloaddition reaction: regioselective high-yielding synthesis of fully decorated 1,2,3-triazoles.
TL;DR: An enolate-mediated organocatalytic azide-ketone [3+2]-cycloaddition (OrgAKC) reaction of a variety of enolizable arylacetones and deoxybenzoins with aryL azides was developed for the synthesis of fully decorated 1,4-diaryl-5-methyl(alkyl)-1,2,3-triazoles in excellent yields with high regioselectivity.
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.