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

Kaushik Chander Prakash (Guru Jambheshwar University of Science & Technology, Department of Chemistry, Hisar, Haryana, India)
Kumar Krishan (Guru Jambheshwar University of Science & Technology, Department of Chemistry, Hisar, Haryana, India)
Kumar Devinder (Guru Jambheshwar University of Science & Technology, Department of Chemistry, Hisar, Haryana, India)
Mor Satbir (Guru Jambheshwar University of Science & Technology, Department of Chemistry, Hisar, Haryana, India)
Kumar Ashwani (Guru Jambheshwar University of Science & Technology, Department of Pharmaceutical Sciences, Hisar, Haryana, India)
Kumar Jindal Deepak (Guru Jambheshwar University of Science & Technology, Department of Pharmaceutical Sciences, Hisar, Haryana, India)

Regioselective synthesis of some amide–ether-linked 1,4-disubstituted 1,2,3-triazoles was realized via the 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 their in vitro antimicrobial activity against Bacillus subtilis, Staphylococcus aureus (Gram-positive bacteria), Pseudomonas aeruginosa, Escherichia coli (Gram-negative bacteria), Candida albicans and Aspergillus brasiliensis (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 the tested microbial strains. The docking simulation of the broad spectrum microbicidal disubstituted 1,2,3-triazole 13d into the active site of E. coli type II topoisomerase, DNA gyrase B enzyme was also investigated.

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