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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Book ChapterDOI
Copper(I)–Acetylides: Access, Structure, and Relevance in Catalysis
TL;DR: The most current applications of copper-I-mediated reactions of alkynes involving copper(I)acetylide are presented in this article, focusing on the mechanistic understanding of these transformations and the effect of the metal acetylides in the reaction pathways.
Journal ArticleDOI
Three-component assembly of 5-halo-1,2,3-triazoles via aerobic oxidative halogenation
TL;DR: In this paper, an effective synthetic protocol for 5-halo-1,2,3-triazoles was developed by novel TBDMSCl ( tert-butyldimethylsilyl chloride)-activated aerobic oxidative halogenations.
Journal ArticleDOI
Copper fluorapatite assisted synthesis of new 1,2,3-triazoles bearing a benzothiazolyl moiety and their antibacterial and anticancer activities
Sambhaji T. Dhumal,Amarsinh R. Deshmukh,Kiran R. Kharat,Bhaskar R. Sathe,Santosh S. Chavan,Ramrao A. Mane +5 more
TL;DR: In this paper, a series of new 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)benzo[d]thiazoles were synthesized via a copper fluorapatite (CuFAP) catalysed click reaction.
Journal ArticleDOI
Derivatives of grindelic acid: from a non-active natural diterpene to synthetic antitumor derivatives
Guillermo Federico Reta,Alejandra I. Chiaramello,Celina García,Leticia G. Leon,Víctor S. Martín,José M. Padrón,Carlos E. Tonn,Osvaldo J. Donadel +7 more
TL;DR: Using several reactions that include homologations and asymmetric epoxidations as well as Ugi and Huisgen couplings, a small focused library of new derivatives from the labdane-type diterpene grindelic acid were generated and proved to be the most active product in all cell lines tested.
Journal ArticleDOI
Triazolopyridyl ketones as a novel class of antileishmanial agents. DNA binding and BSA interaction.
Rosa Adam,Pablo Bilbao-Ramos,Sonia López-Molina,Belén Abarca,Rafael Ballesteros,M. Eugenia González-Rosende,M. Auxiliadora Dea-Ayuela,M. Auxiliadora Dea-Ayuela,Gloria Alzuet-Piña +8 more
TL;DR: The triazolopyridine derivative 6 was effective against both spleen and liver parasites forms, while 7 was inactive against liver parasites, and both compounds interact at BSA site I and, to a lesser extent, at site II.
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.