Some new 2,3,6-trisubstituted quinazolinones as potent anti-inflammatory, analgesic and COX-II inhibitors

Abstract

Various 2-(substitutedphenylmethyleneimino)aminoacetylmethylene-3-(2′-substitutedindol-3′-yl)-halosubstituted-4(3H)quinazolinones (5a–5i) and 2-(substituted phenylaminomethyleneacetyl-4′-oxo-1′-thiazolidinyl-3-(2″-substitutedindol-3″-yl) 4(3H)-quinazolinones (6a–6i) have been synthesized in the present studies. The structure of these compounds have been elucidated by elemental (C, H, N) and spectral (IR, 1H NMR and mass) analysis. Furthermore, above said compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic activities and acute toxicity study. Compound 6d was found to be most potent. Compound exihibiting less ulcerogenic liability and ALD50 >2000 mg/kg po.

Some 2-(substitutedphenylmethyleneimino)aminoacetylmethylene-3-(2′-substitutedindol-3′-yl)-halosubstituted-4(3H)quinazolinones (5a–5i) and 2-(substituted phenylaminomethyleneacetyl-4′-oxo-1′-thiazolidinyl-3-(2″-substitutedindol-3″-yl)-4(3H)-quinazolinones (6a–6i) have been synthesized. Compound 2-(o-Methoxyphenylaminomethylacetyl-4′-oxo-1′-thiazolidinyl)-3-(indol-3″-yl)-6-iodo-4(3H)-quinazolinone (6d) was found to be the most potent compound of the present study.