Design, synthesis, characterization, and antibacterial activity of {5-chloro-2-[(3-substitutedphenyl-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanones

• Published in: European journal of medicinal chemistry 2010-06, Vol.45 (6), p.2677-2682
• Main Authors: Rai, Neithnadka Premsai, Narayanaswamy, Venugopala Katharigatta, Govender, Thavendran, Manuprasad, B.K., Shashikanth, Sheena, Arunachalam, Pirama Nayagam
• Format: Article
• Language: English
• Subjects: 1,2,4-Oxadiazoles; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Bacteria - drug effects; Benzophenones - chemical synthesis; Benzophenones - chemistry; Benzophenones - pharmacology; Biological and medical sciences; Drug Design; Magnetic Resonance Spectroscopy; Medical sciences; Pharmacology. Drug treatments; Substituted methanones
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2010.02.021

In the present investigation, a series of novel {5-chloro-2-[(3-(substitutedphenyl)-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanones ( 3a– i) have been synthesized from 5-(chloromethyl)-3-substitutedphenyl-1,2,4-oxadiazole ( 2a– i). The newly synthesized compounds were characterized by IR, NMR ( 1H and 13C), mass spectral and elemental analysis. The title compounds were investigated for in-vitro qualitative (zone of inhibition) and quantitative (MIC) antibacterial activity by agar cup plate and microtitration methods, respectively. The minimum inhibitory concentration and structure activity relationships (SARs) were evaluated. Amongst the synthesized compounds in this series, {5-chloro-2-[(3-(2,5-difluoro-4-methyl-phenyl)-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanone ( 3d) was found to exhibit significant activity with MICs of 21.5, 22.4, 29.8 and 30.6 μg/mL against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Klebsiella pneumoniae, respectively. [Display omitted] In the present investigation, a series of novel {5-chloro-2-[(3-(substitutedphenyl)-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanones (3a– i) have been synthesized, characterized and investigated for qualitative (zone of inhibition) and quantitative (MIC) antibacterial activity.