Synthesis of novel 1,3,4-oxadiazole derivatives and their biological properties.
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). 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 a significant decrease of ulcerogenic activity.
Husain
Asif
A
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University), New Delhi-110062, India. drasifhusain@yahoo.com
Ajmal
Mohammed
M
D019342:Acetic Acid; D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D002351:Carrageenan; D004195:Disease Models, Animal; D015195:Drug Design; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D005260:Female; D007249:Inflammation / Q000139:chemically induced / Q000517:prevention & control; D008297:Male; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D010146:Pain / Q000139:chemically induced / Q000517:prevention & control; D051381:Rats; D017208:Rats, Wistar; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development; D013276:Stomach Ulcer / Q000139:chemically induced; D013329:Structure-Activity Relationship
D000700:Analgesics; D000900:Anti-Bacterial Agents; D000893:Anti-Inflammatory Agents; D010069:Oxadiazoles; D002351:Carrageenan; D019342:Acetic Acid