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 in vitro anticancer activity of 4H-pyrano[2,3-d]pyrimidine−1H-1,2,3-triazole hybrid compounds bearing D-glucose moiety with dual EGFR/HER2 inhibitory activity and induced fit docking study
Nguyen Dinh Thanh,Do Son Hai,Le Thi Huyen,Nguyen Thi Kim Giang,Nguyen Thi Thu Ha,Do Tien Tung,Cao Thi Le,Hoang Thi Kim Van,Vu Ngoc Toan +8 more
TL;DR: In this article , a series of 36 analogs of 4H-pyrano[2,3-d]pyrimidine 8a-zj bearing d-glucose moiety tethered 1,2-3-triazole derivatives, including eighteen new ones, were synthesized by click chemistry between these N-propargyl derivatives and peracetylated dglucopyaranosyl azide, with using [email protected] as a catalyst under ultrasound condition.
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Design, synthesis, and biological evaluation of trizole-based heteroaromatic derivatives as Bcr-Abl kinase inhibitors.
TL;DR: In this paper , a series of compounds with heteroaromatics-trizole scaffold as hinge binding moiety (HBM) were developed as Bcr-Abl inhibitors based on in silico modeling analysis.
Journal ArticleDOI
Silver Mediated Banert Cascade with Carbon Nucleophiles.
TL;DR: In this article, the Mayr nucleophilicity parameter (N) was found to correlate with the reaction efficiency, which enabled the formation of Csp3-Csp2 and Csp 3-CSP3 bonds under otherwise identical conditions from structurally dissimilar nucleophiles.
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Microwave versus conventional synthesis, anticancer, DNA binding and docking studies of some 1,2,3-triazoles carrying benzothiazole
Ateyatallah Aljuhani,Meshal A. Almehmadi,Ibrahim O. Barnawi,Nadjet Rezki,Imran Ali,Imran Ali,Mouslim Messali,Mohamed Reda Aouad +7 more
TL;DR: It was found that almost all the compounds showed good anticancer activities at 400 µg/mL concentration but the compounds 5d and 5h may be potentially anticancer candidates.
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Energetic Materials Based on N-substituted 4(5)-nitro-1,2,3-triazoles
G. T. Sukhanov,Yu. V. Filippova,Yuri V. Gatilov,A. G. Sukhanova,Irina А. Krupnova,Konstantin K. Bosov,Ekaterina V. Pivovarova,Vyacheslav I. Krasnov +7 more
TL;DR: In this paper , the regularities and synthetic potentialities of the alkylation of 4(5)-nitro-1,2,3-triazole in basic media were explored, and new energetic ionic and nitrotriazole-based coordination compounds were synthesized.
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.