Regioselective synthesis, characterization and antimicrobial evaluation of amide-ether linked 1,4-disubstituted 1,2,3-triazoles

Chander Prakash Kaushik, Krishan Kumar, Devinder Kumar, Satbir Mor, Ashwani Kumar, Deepak Kumar Jindal

Abstract


Regioselective synthesis of some amide-ether linked 1,4-disubstituted 1,2,3-triazoles was carried out via copper(I)-catalyzed click reaction of 1-(pr­op-2-ynyloxy)naphthalene, 2-(prop-2-ynyloxy)naphthalene and 1,4-bis(prop-2-ynyloxy)benzene with 2-azido-N-substituted acetamides. The synthesized compounds were characterized by spectral techniques viz. FT-IR, 1H-NMR, 13C-NMR, HRMS and evaluated for in vitro antimicrobial activity against Bacillus subtilis, Staphylococcus aureus (Gram positive bacteria), Pseudomonas aeruginosa, Escherichia coli (Gram negative bacteria), Candida albicans and Aspergillus niger (fungi). Among the synthesized 1,4-disubstituted 1,2,3-tri­azoles, compound 13d displayed excellent antibacterial potential, while, compounds 7d and 13d appeared as potent fungicidal agents against tested microbial strains. The docking simulation of broad spectrum microbicidal disubstituted 1,2,3-triazole 13d into the active site of E. coli topoisomerase II DNA gyrase B enzyme was also investigated.

 


Keywords


click reaction; disubstituted 1,2,3-triazoles; antibacterial activity; antifungal activity

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DOI: http://dx.doi.org/10.2298/JSC160812079K

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