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
Selective Synthesis of 5‐Alkynyl Trisubstituted 1,2,3‐Triazoles from Azides and Alkynes via Photoexcited Copper(I)acetylides
TL;DR: In this paper , a simple and selective synthesis of 5-alkynyl trisubstituted 1,2,3-triazoles under photochemical conditions was reported.
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Triple Action of an Attractive Deep Eutectic Solvent in the Synthesis of Aryl Nitriles and Substituted Triazoles Using a Magnetically Reusable Fe 3 O 4 @SiO 2 @PrNCu Catalyst
TL;DR: In this paper , a green Deep Eutectic Solvent (DES) and Fe3O4@SiO2@PrNCu magnetic catalyst was used to accelerate the catalytic process.
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Imine‐Linked Porous Organic Polymer Gel and Immobilization of Copper(II): Easy Synthesis and Excellent Catalyst for Huisgen [3+2] Cycloaddition Reactions
P. J. Amal Joseph,Pintu K. Kundu +1 more
TL;DR: In this article , a mesoporous organic polymeric gels (POP gels) were made by condensation of a newly synthesized C3-symmetrical azobenzene-based tri-salicylaldehyde building block, 1,3,5-tris(4-((3-formyl-4-hydroxyphenyl)diazenyl)phenyl)benzene (TAzo) with suitable aromatic tri- and di-amines in N,N-dimethylformamide (DMF) at ambient conditions.
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Synthesis and reactivity of 5-hydrazino-3-nitro-1,2,4-triazole (HNT): an amphoteric energetic platform
TL;DR: The first synthesis of 5-hydrazino-3-nitro-1,2,4-triazole (HNT) was described in this article , as a free base from 5-bromo-3,nitro -1, 2,4,4 triazole in three steps.
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Synthesis of New Amide Linked Biphenoloxy 1,2,3-Triazoles as Antitubercular and Antimicrobial Agents
TL;DR: In this article , 1,2,3-triazoles bearing biphenoloxymethyl and acetanilido moieties (5a-5l) have been synthesized, starting from 4-phenylphenol (1) following click chemistry approach.
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.