Synthesis and antibacterial activity of 3-substituted 1-(2-methyl-5-nitrophenyl)-5-oxopyrrolidine derivatives

Abstract

A series of new 1,3-disubstituted pyrrolidinone derivatives bearing triazole, thiazole, thiadiazole, oxadiazole, sulfamoylphenyl, etc., moieties were synthesized from 1-(2-methyl-5-nitrophenyl)-5-oxopyrrolidine-3-carbohydrazide. Reactions of 5-substituted 4-amino-1,2,4-triazole with α-haloketones were investigated leading to the target [1, 2, 4]triazolo[3,4-b][1, 3, 4]thiadiazine derivatives. The synthesized compounds were tested for antibacterial activity against S. aureus, L. monocytogenes, E. coli, and P. aeruginosa. The 1-(2-Methyl-5-nitrophenyl)-5-oxo-N-(3-sulfamoylphenyl)pyrrolidine-3-carboxamide and its 4-sulfamoylphenyl analogue have demonstrated excellent antibacterial activity with MIC and MBC values of 7.8 and 15.6 µg/mL, respectively, against P. aeruginosa and L. monocytogenes.