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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Copper Acetate Catalyzed Regioselective Synthesis of Substituted 1,2,3-Triazoles: A Versatile Azide–Alkene Cycloaddition/Oxidation Approach
TL;DR: A copper acetate catalyzed oxidative cycloaddition reaction of benzyl and aryl azides with terminal and internal olefins that contain electron-withdrawing groups that contain COOR, CONH2, CN, CHO, COR has been developed.
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Novel menadione hybrids: Synthesis, anticancer activity, and cell-based studies.
TL;DR: Flow cytometric analysis revealed that compound 6 can be considered as lead molecule for further development as potent anticancer therapeutic agent and induced apoptotic cell death which was confirmed by Hoechst staining, measurement of mitochondrial membrane potential (ΔΨm) and Annexin‐V‐FITC assay.
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Binaphthyl-1,2,3-triazole peptidomimetics with activity against Clostridium difficile and other pathogenic bacteria
Steven M. Wales,Katherine A. Hammer,Amy McKarral King,Andrew J. Tague,Dena Lyras,Thomas V. Riley,Paul A. Keller,Stephen Pyne +7 more
TL;DR: Copper- and ruthenium-click chemistry facilitated the generation of a 46 compound library for in vitro bioactivity assays, with structure-activity trends over the largest compound subset revealing a clear advantage to triazole-substitution with a linear or branched hydrophobic group.
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Intramolecular cyclization of the antimicrobial peptide Polybia-MPI with triazole stapling: influence on stability and bioactivity.
Beijun Liu,Wei Zhang,Sanhu Gou,Haifeng Huang,Jia Yao,Zhibin Yang,Hui Liu,Chao Zhong,Beiyin Liu,Jingman Ni,Rui Wang +10 more
TL;DR: The design and synthesis of cyclic analogs via click chemistry offer a new strategy for the development of stable antimicrobial agents and provides additional insight into the influence of intramolecular cyclization at various positions on peptide structure and biological activity.
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Dual catalysis by Cu(I): facile single step click and intramolecular C–O bond formation leading to triazole tethered dihydrobenzodioxines/benzoxazines/benzoxathiines/benzodioxepines
TL;DR: In this paper, the synthesis of novel benzodioxines (benzodioxanes), benzoxazines, benzoxathiines and benodioxepines, which feature benzo-condensed six or seven membered rings containing two hetero-atoms attached to a 1,2,3-triazole, was described.
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.