Synthesis of some substituted 4 [3H] Quinazo-linones ofdiverse biological activities

ABSTRACT

The synthesis of 3-[[3-hydroxy-4-methoxyphenyl] and 3-[4-hydroxy-2-methylphenyl]-4[3H]-quinazolinone and their nitroanalogs 2 and 3 is described. Reaction of 2 and 3 with alkyl halides gave the alkoxy derivatives 4 and 7, reaction with alkyl or aryl isocyanates afforded the alkyl or aryl carbamoyloxy derivatives 5 and 8, while reaction with aldehydes yielded the 2-styryl derivatives 6 and 9. Refluxing 3 with secondary amines and formaldehyde produced mannich bases 10. Reaction of 3 with ethyl chloroacetate gave the ethyl phenoxyacetate 11 which upon refluxing with hydrazine hydrate yielded the acid hydrazide 12. Further reaction of 12 with aldehydes or isothiocyanates afforded the hydrazones 13 or the thiosemicarbazides 14, respectively. Cyclization of the latter with chloroacetic acid produced the thiazolidinones 15. Fifteen of the newly synthesized compounds were screened for tranquillizing, anticonvulsant and analgesic activities. Twelve of the tested compounds showed marked activities