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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Synthesis and Insecticidal Evaluation of Novel Phthalic Diamides Containing 1,2,3‐Triazoles via Click Reaction
TL;DR: A series of phthalic diamide derivatives containing 1,2,3-triazole moiety were synthesized using one-pot click chemistry approach and characterized by 1H NMR and HRMS.
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DFT, molecular docking and experimental FT-IR, laser-Raman, NMR and UV investigations on a potential anticancer agent containing triazole ring system
TL;DR: In this article, the experimental FT-IR, Ra, NMR, and UV spectral data along with the theoretical quantum chemical calculations for 5-methyl-1-(4-methylphenyl)-Nʹ-[1-(thiophen-2-yl)ethylidene]-1H-1,2,3-triazole-4-carbohydrazide were investigated in detail.
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Synthesis, Structure and H+/K+‐ATPase Inhibitory Activity of Novel Triazolyl Substituted Tetrahydrobenzofuran Derivatives via One‐pot Three‐component Click Reaction
TL;DR: Eleven triazolyl substituted tetrahydrobenzofuran derivatives were synthesized in high yields as novel H+/K+-ATPase inhibitor via one-pot CuI-catalyzed three-component click reaction of azide, secondary amine and 3-bromopropyne under mild conditions in water.
Journal ArticleDOI
Synthesis and Cytotoxic Activity of New Vindoline Derivatives Coupled to Natural and Synthetic Pharmacophores.
András Keglevich,Leonetta Dányi,Alexandra Rieder,Dorottya Horváth,Áron Szigetvári,Miklós Dékány,Csaba Szántay,Ahmed Dhahir Latif,Attila Hunyadi,István Zupkó,Péter Keglevich,László Hazai +11 more
TL;DR: New Vinca alkaloid derivatives were synthesized to improve the biological activity of the natural alkaloids vindoline and exhibited in vitro antiproliferative activity against human gynecological cancer cell lines with IC50 values in the low micromolar concentration range.
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Transition metal-free steric controlled one-pot synthesis of highly substituted N-amino 1,2,3-triazole derivatives via diazo transfer reaction from β-keto esters
TL;DR: In this article, a simple protocol for the one-pot synthesis of N -amino 1,2,3-triazole from β-keto esters has been described.
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.