Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents.
Some new 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-substituted phenyl-2,3-dihydro-1,3,4-oxadiazoles and 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-substituted phenyl-1,3,4-oxadiazoles have been synthesized and evaluated for antimicrobial activity. Initially, 3-chloro-1-benzo[b]thiophene-2-carbonyl chloride (1) was prepared from cinnamic acid in the presence of chlorobenzene and thionyl chloride. This compound (1) was treated with hydrazine hydrate to afford 3-chloro-1-benzo[b]thiophene-2-carbohydrazine (2) which was further reacted with various aromatic aldehydes to yield hydrazones (3a-h). Further reaction of these hydrazones (3a-h) with acetic anhydride gave 3-acetyl-5-(3-chloro-1-benzo[b]thiophen-2-yl)-2-substituted phenyl-2,3-dihydro-1,3,4-oxadiazoles (4a-h). Reaction of the same compounds (3a-h) in the presence of chloramine-T afforded 2-(3-chloro-1-benzo[b]thiophen-2-yl)-5-substituted phenyl-1,3,4-oxadiazoles (5a-h). The structures of newly synthesized compounds (4a-h) and (5a-h) have been confirmed by spectroscopic techniques such as IR, 1H NMR and elemental analysis. All the compounds were screened for their antibacterial activities against Staphylococcus aureus, Bacillus subtilis. Escherichia coli and Pseudomonas aeruginosa and for antifungal activity against Candida albicans and Asperigillus niger. The compounds exhibited significant antibacterial and moderate antifungal activities. Compounds 4c and 4e were found to be most potent with activities, even better than standard drug ciprofloxacin against S. aureus and B. subtilis.
Department of Pharmaceutical Chemistry, S.D.College of Pharmacy, Barnala-148 101, India. rchawlapharma@yahoo.com
Rakesh
R
Chawla
Anshu
A
Arora
Manoj Kumar
MK
Parameswaran
Prabodh
P
Chan
Der
D
Sharma
Sukumar
S
Michael
Thengungal Kochupappy
TK
Ravi
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects / Q000254:growth & development; D002855:Chromatography, Thin Layer; D052978:Disk Diffusion Antimicrobial Tests; D015195:Drug Design; D005658:Fungi / Q000187:drug effects / Q000254:growth & development; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000494:pharmacology; D017550:Spectroscopy, Fourier Transform Infrared; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D010069:Oxadiazoles