Synthesis and antimicrobial activity of N1-(3-chloro-4-fluorophenyl)-N4-substituted semicarbazone derivatives

A series of 16 N-1-(3-chloro-4-fluorophenyl)-N-4-substituted semicarbazone derivatives were synthesized and subjected to computational pharmacokinetic studies to predict molecular properties. All the title compounds (4a-p) followed the Lipinski "Rule of Five''. The synthesized compounds were characterized by elemental analyses and spectral data and the compounds (4a-p) were evaluated for antimicrobial activities. Among them the compound 2-(4-hydroxybenzylidene)-N-(3-chloro-4-fluorolphenyl) hydrazinecarboxamide (4f) was found to be the most active compound that showed good antibacterial activity while the compound 2-(4-methoxybenzylidene)-N-(3-chloro-4-fluorolphenyl) hydrazinecarboxamide (4g) was moderately active against fungal strains. We have noticed that the compounds, (4f, 4k and 4d) bearing OH and NO2 groups on the phenyl ring at position 4 exhibited good antibacterial activity while compound (4g) bearing OCH3 on the phenyl ring at position 4 exhibited moderate antifungal activity. (C) 2011 Production and hosting by Elsevier B. V. on behalf of King Saud University.