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
Correction: Synthesis of l-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors.
Siddamal Reddy Putapatri,Abhinav Kanwal,Balasubramanian Sridhar,Sanjay K. Banerjee,Srinivas Kantevari +4 more
TL;DR: The key reactions involved are Zn(OTf)2 catalyzed enantioselective alkynylation of L-rhamnose derived azidoaldehyde and deprotection of the acid sensitive 1,2-isopropylidene group followed by in situ intramolecular click-cycloaddition of azidoalkynols.
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Synthesis and anticancer activity evaluation of a quinoline-based 1,2,3-triazoles
TL;DR: A small library of methylthio- or methylseleno-quinolyl-linked 1,4-disubstituted 1,2,3-triazole conjugates has been synthesized from the halogenopropargylthio or halogenOP-PARGylseleno -quinolines through one-pot click reaction as mentioned in this paper.
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Sub 1 nm Poly(acrylic acid)-Capped Copper Nanoparticles for the Synthesis of 1,2,3-Triazole Compounds
TL;DR: The stable, water-soluble, and fluorescent sub 1 nm sized poly(acrylic acid)-capped copper nanoparticles (PAACC NPs) were synthesized using a high-intensity ultrasound sonication method and serve as effective catalysts for the synthesis of 1,2,3-triazoles via click reaction in good yields under mild reaction conditions.
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Topochemical Cycloaddition Reaction between an Azide and an Internal Alkyne.
TL;DR: In this paper , a trisubstituted-1,2,3-triazole linked polycyclitol was synthesized using topochemical azide-alkyne cycloaddition.
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.