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
Design, synthesis, characterization of some new 1,2,3-triazolyl chalcone derivatives as potential anti-microbial, anti-oxidant and anti-cancer agents via a Claisen–Schmidt reaction approach
Manjunatha Bhat,Gundibasappa Karikannar Nagaraja,P Divyaraj,N Harikrishna,K Sreedhara Ranganath Pai,Subhankar Biswas,S K Peethamber +6 more
TL;DR: In this article, a new series of (2E)-1-{1]-1-dichloro-6-methyl-5-(trifluoromethyl)phenyl]-5-methyl 1H-1,2,3-triazol-4-yl]-prop-2-en-1-one (6a-e) was synthesized via a Claisen-Schmidt condensation.
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Synthesis of new pyrazole-1,2,3-triazole dyads
TL;DR: An efficient two-step synthetic methodology of new 5(4)-aryl-4(5)-[3 (5)-(2-hydroxyphenyl)-1 H-pyrazol-5(3)-yl]-1 H -1,2,3-triazole dyads was established as discussed by the authors.
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Facile and direct halogenation of 1,2,3-triazoles promoted by a KX–oxone system under transition metal free conditions
TL;DR: In this paper, a convenient and efficient oxidative halogenation of 4-aryl 1,2,3-triazoles is realized at ambient temperature under transition metal free conditions, using readily available potassium halides (KBr, KCl, and KI) with oxone as an oxidant under mild reaction conditions and halogenated products are obtained in good to excellent yields.
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A new general synthesis of annulated 1,2,3-triazoles using tandem Sonogashira-CuAAC reaction
TL;DR: A number of fused 1,2,3-triazoles have been synthesized efficiently by the palladium(0)-copper(I)-catalyzed intramolecular heteroannulation of 2-/1-azidomethyl-1-/2-bromodihydro-naphthalenes, -arene and -cycloalkenes with terminal alkynes involving tandem Sonogashira coupling-CuAAC reaction.
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1,2,3-Triazole tethered 1,2,4-trioxanes: Studies on their synthesis and effect on osteopontin expression in MDA-MB-435 breast cancer cells.
TL;DR: It is observed that artemisinin did not show appreciable OPN downregulation in MDA-MB-435 cancer cells, but dihydroart Artemisinin (DHA) and some synthetic 1,2,4-trioxane monomers and dimers showed downregulation of OPN expression, therefore, these compounds may act as an anti-metastatic agent in controlling breast cancer cells metastasis.
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.