Open AccessSynthesis and antimicrobial activity of N1-(3-chloro-4-fluorophenyl)-N4-substituted semicarbazone derivatives
Author(s) -
Mohamed Jawed Ahsan,
Mohammad Amir,
Mohamed Afroz Bakht,
Jeyabalan Govinda Samy,
Mohamed Zaheen Hasan,
Md. Shivli Nomani
Publication year - 2011
Publication title -
arabian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.789
H-Index - 70
eISSN - 1878-5379
pISSN - 1878-5352
DOI - 10.1016/j.arabjc.2011.09.012
Subject(s) - chemistry , semicarbazone , antimicrobial , lipinski's rule of five , antibacterial activity , ring (chemistry) , antifungal , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , bacteria , biochemistry , medicine , genetics , dermatology , biology , in silico , gene
A series of 16 N1-(3-chloro-4-fluorophenyl)-N4-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
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