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 antifungal activity of the novel triazole derivatives containing 1,2,3-triazole fragment
Shichong Yu,Nan Wang,Nan Wang,Xiaoyun Chai,Baogang Wang,Hong Cui,Qingjie Zhao,Yan Zou,Qingyan Sun,Qing-Guo Meng,Qiuye Wu +10 more
TL;DR: The MIC80 values indicate that the target compounds 1a–r showed higher activities against nearly all the fungi tested to some extent except against Aspergillus fumigatus.
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Alumina‐Supported Copper Iodide: An Efficient and Recyclable Catalyst for Microwave‐Assisted Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles via Three‐Component Reaction in Water
TL;DR: In this article, a one-pot procedure for the synthesis of 1,4-disubstituted 1,2,3-triazoles by a three-component reaction of allyl or benzyl halides, sodium azide, and terminal alkynes over a neutral alumina-supported copper iodide catalyst has been developed.
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C-H functionalization via electrophotocatalysis and photoelectrochemistry: complementary synthetic approach
TL;DR: In this article, the authors describe some of the recent developments in PEC-driven organic synthesis by combining electrochemistry and photoredox catalysis in a single system, which can achieve reactions that previous methodologies would find difficult or impossible, and it can do so in an environmentally friendly, energy saving manner with high atom and step economies.
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C5-curcuminoid-4-aminoquinoline based molecular hybrids: design, synthesis and mechanistic investigation of anticancer activity
Shamseer Kulangara Kandi,Sunny Manohar,Christian E. Vélez Gerena,Beatriz Zayas,Sanjay V. Malhotra,Diwan S. Rawat +5 more
TL;DR: This study has identified a set of covalent hybridization of curcumin and 4-aminoquinolines that showed excellent growth inhibition at nano-molar concentrations and showed apoptotic induction as a cause for their displayed anticancer activity.
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Ecological Recycling of a Bio‐Based Catalyst for Cu Click Reaction: a New Strategy for a Greener Sustainable Catalysis
TL;DR: In this article, a novel bio-sourced ecocatalysts for the Cu catalyzed azide-alkyne cycloaddition reaction (CuAAC) are presented.
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.