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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Towards click chemistry: Multicomponent reactions via combinations of name reactions
TL;DR: In this article, the importance of incorporation of name reactions in the sequential cascade reaction in which significantly decreasing the number of steps towards an ideal and practical multi-step synthesis of natural products as well showing virtually all the advantages already mentioned for click chemistry.
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Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity
Ratchanok Pingaew,Prasit Mandi,Chanin Nantasenamat,Supaluk Prachayasittikul,Somsak Ruchirawat,Somsak Ruchirawat,Somsak Ruchirawat,Virapong Prachayasittikul +7 more
TL;DR: A novel series of N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-triazoles containing triazole moiety were designed and synthesized through rational cycloadditions using the modified Pictet-Spengler reaction and the Click chemistry and showed stronger anticancer activity against HepG2 cells than that of the etoposide.
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Synthesis, characterization and antimicrobial activity of 4-((1-benzyl/phenyl-1 H -1,2,3-triazol-4-yl)methoxy)benzaldehyde analogues
TL;DR: A diverse series of 4-((1-benzyl/phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde analogues has been synthesized in good yield by the click reaction between 4-O-propargylated benzaldehyde and various organic bromides/azides and exhibited good-to-excellent antimicrobial activity.
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Alkynyl Phosphonate DNA: A Versatile “Click”able Backbone for DNA-Based Biological Applications
TL;DR: The results demonstrate that triazolylphosphonate ODNs are versatile additions to the oligonucleotide chemist's toolbox relative to designing new biological research reagents.
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Synthesis of Novel Triazole‐incorporated Isatin Derivatives as Antifungal, Antitubercular, and Antioxidant Agents and Molecular Docking Study
Mubarak H. Shaikh,Dnyaneshwar D. Subhedar,Firoz A. Kalam Khan,Jaiprakash N. Sangshetti,Laxman Nawale,Manisha Arkile,Dhiman Sarkar,Bapurao B. Shingate +7 more
TL;DR: A library of 1-2,3-triazoles efficiently prepared via click chemistry and evaluated for their antifungal, antitubercular, antioxidant, cytotoxicity, molecular docking and ADME prediction.
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.