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
More filters
Journal ArticleDOI
Theoretical insights into the synthesis reaction mechanism of 1,2,3-triazole based on sakai reaction
TL;DR: In this article, the DFT calculations were carried out to study the reaction mechanism of Sakai reaction and two different paths for Sakai Reaction were revealed by their calculations, depending on the type of amines, for the triazolamine, an H atom must transfer from the amines to the diazine synchronously when the new C-N bond is formed.
Journal ArticleDOI
Bioprospecting of Nitrogenous Heterocyclic Scaffolds with Potential Action for Neglected Parasitosis: A Review.
Sonaly Lima Albino,Jamire Muriel Da Silva,Michelangela Suelleny de Caldas Nobre,Yvnni Maria Sales de Medeiros E Silva,Mirelly Barbosa Santos Santos,Rodrigo Santos Aquino de Araújo,Maria do Carmo Alves de Lima,Martine Schmitt,Ricardo Olímpio de Moura +8 more
TL;DR: It is concluded that despite the great biodiversity on the planet, little attention has been given to certain neglected tropical diseases, especially those that reach countries with a high poverty rate.
Journal ArticleDOI
N,N-Dibenzyl-1-(1-[(4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)]-1H-1,2,3-triazol-4-yl)methanamine
TL;DR: In this paper, the title compound, N,N-dibenzyl-1-(1-[(4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)]-1H-1,2,3-triazol 4-yl]methanamine was synthesized in high yield by 1,3dipolar cycloaddition reaction of 4-(azidomethyl)-4-myl)-2.
Journal ArticleDOI
Accelerating effect of triazolyl and related heteroaryl substituents on SNAr reactions: evidence of hydrogen-bond stabilized transition states.
TL;DR: The experimentally determined solvent effect provides further support for the rationale for the remarkable accelerating effect of 1,2,3-triazolyl substituents on SNAr reactions, which was utilized to achieve an ortho-selective substitution on a difluoroarene substrate.
References
More filters
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.