A. Husain, M. Ajmal
Jun 1, 2009
Citations
1
Influential Citations
103
Citations
Quality indicators
Journal
Journal name not available for this finding
Abstract
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. Sinteza i djelovanje novih derivata 1,3,4-oksadiazola Reakcijom 3-(4-brombenzoil)propionske kiseline (3) i aril hidrazida (2a-n) u prisutnosti fosforovog oksiklorida, sintetizirana je serija novih derivata 2-[3-(4-bromfenil)propan-3-on]-5-(supstituiranih fenil)-1,3,4-oksadiazola (4a-n) s ciljem da se dobiju spojevi s boljim protuupalnim i analgetskim, a manjim elcerogenim djelovanjem. Struktura sintetiziranih spojeva potvrđena je IR, 1H NMR i masenom spektroskopijom. Ispitano je protuupalno, analgetsko, ulcerogeno i antibakterijsko djelovanje spojeva 4a-n. Antibakterijsko djelovanje izraženo je kao minimalna inhibitorna koncentracija (MIC). Nekoliko spojeva imalo je značajno protuupalno i analgetsko djelovanje, nekoliko prilično antibakterijsko djelovanje, a svi su imali vrlo slabo ulcerogeno djelovanje. Rezultati ukazuju da ciklizacija karboksilne skupine u spoju 3 u 1,3,4-oksadiazol dovodi do povećanja protuupalnog i analgetskog, a do smanjenja ulcerogenog djelovanja.