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
Ciprofloxacin-Tethered 1,2,3-Triazole Conjugates: New Quinolone Family Compounds to Upgrade Our Antiquated Approach against Bacterial Infections
TL;DR: In this article , a new ciprofloxacin series containing 1,2,3-triazole conjugates was designed, synthesized, and well characterized using modern analytical techniques by reacting diversified anilines with CIPROFLOACIN obtained from cipprofloxACin hydrochloride.
Journal ArticleDOI
Fluorescent Analogues of FRH Peptide: Cu(II) Binding and Interactions with ds-DNA/RNA
TL;DR: KA(triazole)coumarin can be considered as the shortest peptidoid sequence with highly sensitive fluorescent and chiral CD response for Cu2+ cation, encouraging further studies with other metal cations.
Journal ArticleDOI
Recent Progress in the Synthesis of Homogeneous Erythropoietin (EPO) Glycoforms.
TL;DR: The scope of this minireview is to summarise the recent advances in the chemical and semisyntheses of homogeneousEPO glycoforms, highlighting the versatile approaches to the preparation and structural manipulations of the carbohydrate chains incorporated into synthetic EPO glycoproteins.
Journal ArticleDOI
An efficient synthetic route towards novel furo- and thieno-triazolopyridines
Book ChapterDOI
Recent Progress in the Chemistry of Tri-substituted Triazole via [3 + 2] Cycloaddition of Azide and Double Bond: An Overview
TL;DR: In this paper, the first synthesis of tri-substituted triazoles was achieved by Huisgen via azide-alkyne cycloaddition and the remarkable achievement in triazole-based pharmacology promoted ample interest in the discovery of new synthetic methods and catalysts for the synthesis of this miraculous scaffold.
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.
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.