Synthesis, antibacterial activity, and quantitative structure–activity relationships of new (Z )-2-(nitroimidazolylmethylene)-3(2H2H)-benzofuranone derivatives

A new series of (Z  )-2-(1-methyl-5-nitroimidazole-2-ylmethylene)-3(2H2H)-benzofuranones (11a–p) and (Z  )-2-(1-methyl-4-nitroimidazole-5-ylmethylene)-3(2H2H)-benzofuranones (12a–m) were synthesized and assayed for their antibacterial activity against Gram-positive and Gram-negative bacteria. Most of the 5-nitroimidazole analogues (11a–p) showed a remarkable inhibition of a wide spectrum of Gram-positive bacteria (Staphylococcus aureus, Streptococcus epidermidis, MRSA, and Bacillus subtilis) and Gram-negative Klebsiella pneumoniae, whereas 4-nitroimidazole analogues (12a–m) were not effective against selected bacteria. The quantitative structure–activity relationship investigations were applied to find out the correlation between the experimentally evaluated activities with various parameters of the compounds studied. The QSAR models built in this work had reasonable predictive power and could be explained by the observed trends in activities.

Graphical abstractSynthesis, biological evaluation, and QSAR analysis of a novel class of (ZZ)-2-(nitroimidazolylmethylene)-3(2H2H)-benzofuranone derivatives (11a–p and 12a–m) as antibacterial agents are described.Figure optionsDownload full-size imageDownload as PowerPoint slide