Synthesis of 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent

N-Chloroacetyl-5-bromoanthranilic acid (1), 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-chloromethyl-6-bromoquinazolin-4-one (2), 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-hydrazinomethyl-6-bromoquinazolin-4-one (3), 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-substitutedbenzylidene aminomethyl-6-bromoquinazolin-4-ones (4–11), 2-[(4′-oxo-3′-chloro-2′-phenylazetidin-1′-yl)aminomethyl]-3-[4″-(p-chlorophenyl)thiazol-2″-yl]-6-bromoquinazolin-4-ones (12–19) and 2-(4′-oxo-2′-phenyl-thiazolidin-3′-yl-aminomethyl)- 3-[4″-(p-chlorophenyl)-thiazol-2″-yl]-6-bromoquinazolin-4-ones (20–27) have been synthesized. All the compounds have been screened for their anti-inflammatory and analgesic activities at the dose of 50 mg/kg po. Compound 21 showed maximum anti-inflammatory (38.35%) and analgesic (37.36%) activities. Compound 21 was also tested for ulcerogenic activity and the UD50 value was found to be 195.6 mg/kg po. The structure of all compounds has been evaluated by elemental analysis (C, H, N) and spectral analysis (IR, 1H NMR and mass spectrometry).

Synthesis and characterization of some new bromo-quionazolin-4-one derivatives which have been found to possess anti-inflammatory and analgesic activities. The most active compound is 21. It shows better anti-inflammatory and analgesic activities at the does of 100 mg/kg po.Figure optionsDownload as PowerPoint slide