Acta Pharm. 59 (2009) 223-233
Original research paper
Synthesis of novel 1,3,4-oxadiazole derivatives and studies for their biological properties
ASIF HUSAIN and MOHAMMED AJMAL
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University), New Delhi-110062, India
Accepted March 5, 2009
A novel series of 2-[3-(4-bromophenyl)propan-3-one]-5-(substituted phenyl)-1,3,4-oxadiazoles (4a-n) have been synthesized from 3-(4-bromobenzoyl)propionic acid (3) with the aim to get better anti-inflammatory and analgesic agents with minimum or without side effects (ulcerogenicity). Compound 3 was reacted with several aryl acid hydrazides (2a-n) in phosphorous oxychloride to obtain the title compounds. Structures of the synthesized compounds were supported by means of IR, 1H NMR and mass spectroscopy. Title compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic and antibacterial activities. Antibacterial activity was expressed as the corresponding minimum inhibitory concentration (MIC) values. A fair number of compounds were found to have significant anti-inflammatory and analgesic activities, while a few compounds showed appreciable antibacterial activity. The newly synthesized compounds showed very low ulcerogenic action. The findings of the present study indicate that cyclization of the carboxylic group of 3 into novel 1,3,4-oxadiazole nucleus resulted in increased anti-inflammatory and analgesic activities with significant decrease of ulcerogenic activity.
Keywords: 1,3,4-oxadiazoles, aroylpropionic acid, anti-inflammatory, analgesic activity, antibacterial activity