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
Role of linkers in tertiary amines that mediate or catalyze 1,3,5-triazine-based amide-forming reactions.
Masanori Kitamura,Fumitaka Kawasaki,Kouichi Ogawa,Shuichi Nakanishi,Hiroyuki Tanaka,Kohei Yamada,Munetaka Kunishima +6 more
TL;DR: Ligand catalysts are synthesized, including a 1,2,3-triazolyl linker that connects a protein ligand to a trimethylamine moiety, and it is found that fluorescent-labeling of a targeting protein using the lig and catalysts proceeded in good yields.
Journal ArticleDOI
Aryne approach towards 2,3-difluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles
Dmitry S. Kopchuk,Dmitry S. Kopchuk,I. L. Nikonov,Grigory V. Zyryanov,Grigory V. Zyryanov,Emiliya V. Nosova,Emiliya V. Nosova,Igor S. Kovalev,Pavel A. Slepukhin,Vladimir L. Rusinov,Vladimir L. Rusinov,Oleg N. Chupakhin,Oleg N. Chupakhin +12 more
TL;DR: In this article, the reaction between 3-(2-pyridyl)-1,2,4-triazines and in situ generated 4,5-difluorobenzyne in toluene affords 2,3-Difluoro-10-(1H-1, 2, 3-triazol-1-yl)pyrido[1.2-a]indoles.
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N-2-Aryl-1,2,3-Triazoles: A Novel Class of Blue Emitting Fluorophores-Synthesis, Photophysical Properties Study and DFT Computations
TL;DR: The experimental absorption and emission of the novel fluorescent triazolyl derivatives were compared with the theoretical data obtained by DFT and TD-DFT computations and they are well in agreement with each other.
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Synthesis of functionalized 1,2,3-triazoles using Bi2WO6 nanoparticles as efficient and reusable heterogeneous catalyst in aqueous medium
Banoth Paplal,Sakkani Nagaraju,Veerabhadraiah Palakollu,Sriram Kanvah,B. Vijaya Kumar,Dhurke Kashinath +5 more
TL;DR: In this paper, a regioselective synthesis of functionalized triazoles via Bi2WO6 nanoparticles mediated 1,3-dipolar cycloaddition reactions of β-nitrostyrenes, phenylacetylene and chalcones with azides (80 °C, 2-6 h) in water was reported.
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Polyoxomolybdate-stabilized Cu2O nanoparticles as an efficient catalyst for the azide–alkyne cycloaddition
Mojtaba Amini,Hadi Naslhajian,Hadi Naslhajian,S. Morteza F. Farnia,Hee Kyoung Kang,Sanjeev Gautam,Keun Hwa Chae +6 more
TL;DR: In this paper, a simple methodology for the stabilization of Cu2O nanoparticles of size 10-30 nm on the polar pore surface of the polyoxomolybdate (NH4)12[Mo36(NO)4O108(H2O)16] ({Mo36}).
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.