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Synthesis, reactions and biological activity of 3-arylidene-5-(4-methylphenyl)-2(3H)-furanones?

Husain Asif (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi, India)
Alam Mumtaz M. (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi, India)
Siddiqui Nadeem (Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi, India)

3-Arylidene-5-(4-methylphenyl)-2(3H)-furanones 2a-m were prepared from 3-(4-methyl-benzoyl)propanoic acid 1 and several aromatic aldehydes. Some of the selected furanones were reacted with ammonia gas and benzylamine to give corresponding 3-arylidene-1,3-dihydro-5-(4-methylphenyl)-2H-pyrrol- 2-ones 3a-h and 3-arylidene-1-benzyl-1,3-dihydro-5-(4-methylphenyl)-2H- -pyrrol-2-ones 4a-f, respectively, which were characterized on the basis of IR, 1H-NMR, mass spectral data and elemental analysis results. These compounds were tested for their anti-inflammatory and antibacterial activities. The compounds, which showed significant anti-inflammatory activity, were further screened for their analgesic and ulcerogenic activities. Three new compounds (2e, 2h and 4d), out of twenty-seven showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. The antibacterial activity is expressed as the corresponding MIC values.

Keywords: furanone, pyrrolone, anti-inflammatory, analgesic, antibacterial activity