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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Targeting PUMA/Bcl-xL interaction by new specific compounds to unleash apoptotic process in cancer cells
Appala Venkata Ramana Murthy,Vennu Narendar,Nangunoori Sampath Kumar,Pasula Aparna,A. K. D. Bhavani,Fabien Gautier,Sophie Barillé-Nion,Philippe Juin,Paul Mosset,René Grée,Nicolas Levoin +10 more
TL;DR: The first examples of small molecules able to disrupt the nanomolar interaction between the pro-apoptotic protein PUMA and its anti-APoptotic counterpart BcL-xL in malignant cells are described and a rationale to this result is proposed.
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A facile method for the synthesis of dihydroquinoline-azide from the Lewis acid-catalyzed reaction of alkylidenecyclopropanes with TMSN3.
Mintao Chen,Yin Wei,Min Shi +2 more
TL;DR: A facile synthetic method for the formation of dihydroquinoline-azide from alkylidenecyclopropanes and TMSN3 under the catalysis of a Lewis acid has been developed, and a number of azide-containing compounds can be instantly accessed in moderate to good yields.
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Cu Nano particles immobilized on silk-fibroin as a green and biodegradable catalyst for copper catalyzed azide-terminal, internal alkynes cycloaddition
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1,3-Dipolarna cikloadicija (I. dio): Dobivanje 1,2,3-triazolnih derivata u nukleozidnoj kemiji
TL;DR: Bakrom katalizirana Huisgenova 1, 3-dipolarna cikloadicija azida i terminalnih alkina kojom regioselektivno nastaju 1, 4-disupstituirani 1, 2, 3 triazoli cesto je primjenjivana metoda sintetske organske kemije as mentioned in this paper.
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Getting insights of molecular interactions for potential drug candidates against S. aureus: Pharmacophore modeling, molecular screening and docking studies.
Shubhangi,Avijit Kumar Paul +1 more
TL;DR: This study enables to excavate pre-existing molecules, which have not been explored till date against this pathogenic strain of bacteria, but can definitely be used as alternatives to resistant drugs.
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.
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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.