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

Chander Kaushik, Krishan Kumar, Devinder Kumar, Satbir Mor, Ashwani Kumar, Jindal Kumar
2017 Journal of the Serbian Chemical Society  
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, 1 H--NMR, 13 C-NMR, HRMS and evaluated for their in vitro antimicrobial activity against Bacillus subtilis, Staphylococcus aureus
more » ... cus 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. Извршена је региоселективна синтеза амид-етар 1,4-дисупституисаних 1,2,3-триазола преко бакар(I)-катализоване "клик" реакције 1-(проп-2-инилокси)нафталена, 2-(проп-2-инилокси)нафталена или 1,4-бис(проп-2-инилокси)бензена са 2-азидо-N-супституисаним ацетамидима. Синтетисана једињења окарактерисана су FT-IR, 1 H-NMR и 13 C-NMR спектроскопијама и HRMS масеном спектрометријом и испитана је њихова in vitro антимикробна активност према Bacillus subtilis, Staphylococcus aureus (Грам-пози-
doi:10.2298/jsc160812079k fatcat:wpn2c3euanhx5kh4djcby2okpy