Abstract
3-Substitutedphenyl-2-bromomethyl-6-substituted quinazolin-4(3H)-ones (7-10) were treated with hydrazine hydrate to give 3-substitutedphenyl-2-hydrazinomethyl-6-substituted quinazolin-4(3H)-ones (11-14). Compounds 11-14 were condensed with various aldehydes to afford 2-substitutedbenzylidene hydrazinomethyl-3-substitutedphenyl-6-substituted quinazolin-4(3H)-ones (15-22). Cycloaddition of compounds 15-22 with thioglycolic acid and triethylamine / chloroacetyl chloride yielded 2-[(4’-oxo-2’ -substitutedphenyl-thiazolidin-3’-yl)-aminomethyl]-3-substitutedphenyl-6-substituted quinazolin-4(3H)- ones (23-30) and 2-[(4’-oxo-3’-chloro-2’-substitutedphenylazetidin-1’-yl)-aminomethyl]-3- substitutedphenyl-6-substituted quinazolin-4(3H)-ones (31-38), respectively. The structures of these compounds have been elucidated by elemental (C, H, N) and spectral (IR, 1H-NMR) analysis. All the above mentioned compounds were evaluated for their anti-inflammatory activity, ulcerogenic activity and acute toxicity study. Compound 27 was found to be most potent amongst all the newly synthesized compounds. This compound also exhibits less ulcerogenic activity and ALD50 is >2000 mg kg-1 p.o.
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