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 of sorafenib analogues incorporating a 1,2,3-triazole ring and cytotoxicity towards hepatocellular carcinoma cell lines
Sarinya Palakhachane,Yuwaporn Ketkaew,Natthaya Chuaypen,Jitnapa Sirirak,Jutatip Boonsombat,Somsak Ruchirawat,Pisit Tangkijvanich,Apichart Suksamrarn,Panupun Limpachayaporn +8 more
TL;DR: A series of 1,2,3-triazole-containing Sorafenib analogues, in which the aryl urea moiety of the original 1, 2,3 triazole moiety was replaced with a 1 2, 3-Triazole ring linking a substituted phenoxy fragment, were prepared successfully via Huisgen 1, 3dipolar cycloaddition and nucleophilic aromatic substitution.
Book ChapterDOI
Click Chemistry in Medicinal Chemistry for Comprehensive Medicinal Chemistry III
P. Thirumurugan,K. Jozwiak +1 more
TL;DR: This chapter is discussing briefly more than 100 lead structures to access information about the active and inhibition fingerprints toward the development of potential drug candidate to deal the unanswered diseases.
Journal ArticleDOI
Combined NMR Spectroscopy and Quantum-Chemical Calculations in Fluorescent 1,2,3-Triazole-4-carboxylic Acids Fine Structures Analysis
TL;DR: In this paper , the optical properties of 2-aryl-1,2,3-triazole acids and their sodium salts were investigated in different solvents (1,4-dioxane, dimethyl sulfoxide DMSO, methanol MeOH) and in mixtures with water.
Journal ArticleDOI
Research for the Reaction of Base-Catalyzed Selective Hydrogen- Deuterium Exchange in Mono-1-substituted 1,2,3-Triazoles
Journal ArticleDOI
Copper-Mediated Intramolecular Interrupted CuAAC Selanylation.
Wystan K.O. Teixeira,Danilo Yano de Albuquerque,Julio Zukerman-Schpector,Diego Seckler,Daniel S. Rampon,Ricardo S. Schwab +5 more
TL;DR: In this paper , a copper-mediated domino CuAAC intramolecular selanylation for the synthesis of unprecedented fused benzo[4,5]selenazolo[3,2-c][1,2,3]triazoles from 1,2bis(2-azidoaryl)diselenides and terminal alkynes under microwave irradiation is described.
References
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Journal ArticleDOI
A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
Journal ArticleDOI
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.
Journal ArticleDOI
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.
Journal ArticleDOI
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.
Journal ArticleDOI
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.