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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Design, Synthesis, Biological Evaluation, and Docking Studies of (S)-Phenylalanine Derivatives with a 2-Cyanopyrrolidine Moiety as Potent Dipeptidyl Peptidase 4 Inhibitors
TL;DR: Biological evaluation revealed that most tested compounds were potent dipeptidyl peptidase 4 (DPP‐4) inhibitors; among them, the cyclopropyl‐substituted phenylalanine derivative 11h displayed the most potent DPP‐4 inhibitory activity.
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Synthesis, characterization and catalytic properties of a new binuclear copper(II) complex in the azide–alkyne cycloaddition
TL;DR: A binuclear copper(II)-oxalate complex containing 2,9-dimethyl-1,10-phenanthroline (dmp) was synthesized via a simple and one-pot reaction as mentioned in this paper.
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Synthesis of some novel orcinol based coumarin triazole hybrids with capabilities to inhibit RANKL-induced osteoclastogenesis through NF-κB signaling pathway.
Boddu Rama Krishna,Boddu Rama Krishna,Dinesh Thummuri,V.G.M. Naidu,Sistla Ramakrishna,Sistla Ramakrishna,Uppuluri Venkata Mallavadhani,Uppuluri Venkata Mallavadhani +7 more
TL;DR: Molecular mechanism studies demonstrated that compound 4d exhibited dose dependent inhibition of RANKL-induced osteoclastogenesis by suppression of the NF-kB pathway, which makes it a promising candidate for further optimization to develop as a potent anti-osteoporotic agent.
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Synthesis, characterization and evaluation of antibacterial activity of (E)-N'-(substituted benzylidene)-2-(2-fluorobenzyl)-5-ethyl-2H-1,2,3-triazole-4-carbohydrazides.
TL;DR: The exploration is to produce some novel biologically active triazole 4-carbohydrazide derivatives by synthesizing newly synthesized compounds characterized and confirmed by spectral data and were screened for anti-bacterial activity.
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Salophen Copper(II) Complex-Assisted Click Reactions for Fast Synthesis of 1,2,3-Triazoles Based on Naphthalene-1,4-dione Scaffold, Antibacterial Evaluation, and Molecular Docking Studies.
TL;DR: The salophen copper(II) complex was successfully used for the efficient synthesis of new 1,2,3‐triazoles based on the naphthalene‐1,4‐dione scaffold and was screened for their in vitro antibacterial activities and were subjected to molecular docking studies.
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.