Results
Title

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

Authors

KAUSHIK, CHANDER PRAKASH; KUMAR, KRISHAN; KUMAR, DEVINDER; MOR, SATBIR; KUMAR, ASHWANI; JINDAL, DEEPAK KUMAR

Abstract

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.

Subjects

REGIOSELECTIVITY (Chemistry); TRIAZOLES; AMIDES; NAPHTHALENE; BACILLUS subtilis

Publication

Journal of the Serbian Chemical Society, 2017, Vol 82, Issue 9, p995

ISSN

0352-5139

Publication type

Academic Journal

DOI

10.2298/JSC160812079K