Drug design based on the principle of conjunction: synthesis, characterization and antihyperglycemic activity study of 3- [2- (3- aroyl- 2, 4- diphenyl- 3 , 4- dihydro- 2h [1, 3] oxazino [5, 6-h] quinolin- 6- yl) ethyl] 2- phenyl- quinazolin- 4(3h)- ones

Abstract

Reaction of anthranilic acid with an excess equivalent of benzoyl chloride in dry pyridine afforded 2-phenyl-4H-benzo [d] [1, 3] oxazin-4-one (I) which on reaction with β-aminoethanol (cholamine) in pyridine solvent yielded 3-(2-hydroxyethyl) -2-phenylquinazolin-4(3H)-one (II). When (II) was reacted with 8-hydroxyquinoline (oxine) in conc. H2SO4, 3-[2-(8-hydroxy-quinolin-5-yl) ethyl] 2-phenylquinazolin -4(3H)-one (III) was obtained which on reaction with primary aromatic amines and excess of aromatic aldehydes furnished 3- [2-(3-benzoyl-2, 4-diphenyl-3, 4-dihydro-2H-[1, 3] oxazino [5, 6-h] quinazolin-6yl) ethyl-2-phenyl-quinazolin -H(3H)-ones (IV). The target compounds (IV) and the intermediates (III) were evaluated for their antihyperglycemic activity in sucrose loaded rat models.