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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A Click Reaction Enabled by Phosphorus-Oxygen Bond for Synthesis of Triazoles
Ankita Bal,Prasenjit Mal +1 more
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A brief survey on the application of metal-catalyzed azide–alkyne cycloaddition reactions to the synthesis of ferrocenyl-x-1,2,3-triazolyl-R (x = none or a linker and R = organic entity) compounds with anticancer activity
TL;DR: In this paper , the authors highlight the importance of metal-catalyzed azide-alkyne cycloaddition reactions in the synthesis of ferrocenyl-x-1,2,3-triazolyl-R compounds with anticancer activity.
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Synthesis and Antitubercular Activity of 4,5-Disubstituted N1-(5′-deoxythymidin-5′-yl)-1,2,3-triazoles
Rajesh Kumar,Rajesh Kumar,Devla Bimal,Kavita,Manish Kumar,Divya Mathur,Jyotirmoy Maity,Sunil K. Singh,Meganathan Thirumal,Ashok K. Prasad +9 more
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Preparation and performance of polyether elastomer with a combination of polyurethane and polytriazole
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Synthesis of Triazole-Containing Furanosyl Nucleoside Analogues and Their Phosphate, Phosphoramidate or Phoshonate Derivatives as Potential Sugar Diphosphate or Nucleotide Mimetics
Andreia Fortuna,Paulo J. Costa,M. Fátima M. Piedade,M. Fátima M. Piedade,M. Conceição Oliveira,Nuno M. Xavier +5 more
TL;DR: The synthesis of stable and potentially bioactive xylofuranosyl nucleoside analogues and potential sugar diphosphate or nucleotide mimetics comprising a 1,2,3-triazole moiety is reported.
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.