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 Novel Oxazolo[4,5-b]pyridine-2-one based 1,2,3-triazoles as Glycogen Synthase Kinase-3β Inhibitors with Anti-inflammatory Potential.
Mushtaq A. Tantray,Imran Khan,Hinna Hamid,Mohammad Sarwar Alam,Sadiq Umar,Yakub Ali,Kalicharan Sharma,Firasat Hussain +7 more
TL;DR: A novel series of oxazolo[4,5‐b]pyridine‐2‐one based 1,2,3‐triazoles synthesized by click chemistry approach and evaluated for in vitro GSK‐3β inhibitory activity showed pronounced in vivo anti‐inflammatory activity and tolerance of gastric mucosa to these compounds was confirmed.
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Synthesis and anti-inflammatory activity of novel triazole hybrids of (+)-usnic acid, the major dibenzofuran metabolite of the lichen Usnea longissima
TL;DR: Two triazole analogs can be considered as lead molecules for further fine tuning to make highly potent anti-inflammatory therapeutic agents.
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Metal-free and azide-free synthesis of 1,2,3-triazoles derivatives
TL;DR: In this article, a review of 1,2,3-triazoles under azide-free and metal-free environments is presented, and a collection and compilation of azide free and metal free synthesis methodologies of 1 2 3 triazoles in single podium is provided.
Journal ArticleDOI
A layered double hydroxide, a synthetically useful heterogeneous catalyst for azide−alkyne cycloadditions in a continuous-flow reactor
Sándor B. Ötvös,Sándor B. Ötvös,Ádám Georgiádes,Mónika Ádok-Sipiczki,Rebeka Mészáros,István Pálinkó,Pál Sipos,Ferenc Fülöp,Ferenc Fülöp +8 more
TL;DR: In this paper, a Cu(II)Fe(III)-layered double hydroxide is shown to efficiently catalyze 1,3-dipolar cycloadditions of organic azides to alkynes leading to valuable 1,2,3 triazoles.
Journal ArticleDOI
Synthesis and antifungal activity of novel oxazolidin-2-one linked-1,2,3-triazole derivatives
Alejandra Ramírez-Villalva,Davir González-Calderón,Roxana I. Rojas-García,Carlos González-Romero,Joaquín Tamariz-Mascarúa,Macario Morales-Rodríguez,Nieves Zavala-Segovia,Aydeé Fuentes-Benítes +7 more
TL;DR: A novel mild and eco-friendly synthetic protocol for obtaining β-ketosulfones (adducts to afford compounds 4a-k) from α-brominated carbonyls in an aqueous nanomicellar medium at room temperature is described.
References
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Journal ArticleDOI
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.