Synthesis of some new substituted azetidinonyl and thiazolidinonyl quinazolon-4(3H)-ones as potential non-steroidal anti-inflammatory and analgesic agents

A series of 2-(5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazole-3-ylthio)-N-(substituted benzylidene) acetohydrazides (5a-5l) have been synthesized via condensation of 2-(5-(6-Bromo-2-methyl-4-oxaquinazolin-3 (4H)-yl)-4H-1,2,4-triazole-3-ylthio)acetohydrazide (4) with different aromatic aldehydes. Cycloaddition of thioglycolic acid with 5a-5l yielded 2-[5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazol-3-ylthio]-N-(substituted benzylidene)-4oxothiazolidin-3-yl) acetamides (6a-6l) while compound 5a-5l on treatment with chloro-acetylchloride in the presence of triethylamine are converted into 2-[5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4-triazol-3-ylthio]-N-(3-chloro-2(substituted benzylidene)-4-oxoazetidin-1-yl) acetamides (7a-7l).The structure of all the newly synthesized compounds have been confirmed by elemental analysis and spectral studies (IR, 1 H-NMR and mass spectroscopy).Compounds 5a-5l,6a-6l and 7a-7l 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 2-[5-(6-Bromo-2-methyl-4-oxoquinazolin-3(4H)-yl)-4H-1,2,4triazol-3-ylthio]-N-(3-chloro(2,6-dichloro benzylidene)-4-oxoazetidin-1-yl) acetamide (7g).