Synthesis and Characterization of Substituted Azetidinonyl and Thiazolidinonyl Quinazolin-4 (3H) -ones as Potential NSAIDs

A series of 2-((2-(substituted benzylidene) hydrazinyl methyl)-3-(naphthalene-2-yl) quinazolin-4(3H)-ones (4a-4e) have been synthesized via condensation of 2-(hydrazinyl methyl)-3-(naphthalene-2-yl) quinazolin-4(3H)-one (3) with different aromatic aldehydes. Cycloaddition of thioglycolic acid with (4a-4e) yielded 3-(naphthalene-2-yl)-4-oxo-3, 4-dihydro-quinazolin-2-yl) methyl amino)-2-(substituted phenyl) thiazolidin-4-(3H)ones (5a-5e). while compound (4a-4e) on treatment with chloro-acetylchloride in the presence of triethylamine are converted into 2-((3-chloro-2-(substituted phenyl)-4-oxoazetidin-1-ylamino) methyl)-3-(naphthalene-2-yl) quinazolin-4(3H)-ones (6a-6e). The structure of all the newly synthesized compounds have been confirmed by elemental analysis and spectral studies (IR, 1H-NMR and mass spectroscopy).Compounds (4a-4e, 5a-5e and 6a-6e) have been evaluated for their anti-inflammatory and analgesic activity and were compared with the standard drug phenylbutazone. The most active compound of this series is 6e.