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, and fungicidal evaluation of a series of novel 5-methyl-1H-1,2,3-trizole-4-carboxyl amide and ester analogues.
Zhen-Jun Wang,Gao Yang,Yan-Ling Hou,Cheng Zhang,Shu-Jing Yu,Qiang Bian,Zheng-Ming Li,Wei-Guang Zhao +7 more
TL;DR: The results of the current study show that these 1,2,3-triazole-4-carboxyl amide and ester analogues represent a new type of SDHI that could be used for the development of novel pesticides.
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Bench-Stable 5-Stannyl Triazoles by a Copper(I)-Catalyzed Interrupted Click Reaction: Bridge to Trifluoromethyltriazoles and Trifluoromethylthiotriazoles.
TL;DR: Bench-stable 5-stannyl triazoles are obtained by a copper-catalyzed interrupted click reaction of easily available terminal alkynes and generate diverse 1,4,5-trisubstituted triazole efficiently, which the traditional click reaction is unable to do.
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Recent advances in click chemistry reactions mediated by transition metal based systems
TL;DR: In this paper, a review of the recent progress recorded, over the last five years, by the transition metal catalysts in the development of novel methods and applications in the field of click chemistry reactions is presented.
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1-Phenyl-1H- and 2-phenyl-2H-1,2,3-triazol derivatives: Design, synthesis and inhibitory effect on alpha-glycosidases
Daniel T. G. Gonzaga,Mario Roberto Senger,Fernando de C. da Silva,Vitor F. Ferreira,Floriano P. Silva +4 more
TL;DR: The results demonstrated the potential activity of simple and non-glycosidic triazoles as an important novel class of GIs for the development of drugs to treat Type 2 DM.
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An Overview of Recent Advances in Biomedical Applications of Click Chemistry.
TL;DR: In this article, a review of click reactions is presented, the key aspects, the mechanistic details and merits and demerits of the click reaction, and the recent pharmaceutical applications of click chemistry, ranging from the development of anticancer, antibacterial, and antiviral agents to that of biomedical imaging agents and clinical therapeutics.
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.