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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

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Author(s): Bishnoi A. | Awasthi R. | Pandey V.K. | Tiwari A.K. | Awasthi N.K. | Srivastava K. | Singh S.

Journal: International Journal of Drug Discovery
ISSN 0975-4423

Volume: 1;
Issue: 2;
Start page: 52;
Date: 2009;
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Keywords: Anthranilic acid | Benzoyl chloride | Pharmacophoric moieties Quinazolinones | Diabetes mellitus | Antihyperglycemic activity

ABSTRACT
Reaction of anthranilic acid with an excess equivalent of benzoyl chloride in dry pyridine afforded2- phenyl- 4H- benzo [d] [1, 3] oxazin- 4- one (I) which on reaction with -aminoethanol (cholamine) inpyridine solvent yielded 3- (2- hydroxyethyl) - 2- phenylquinazolin- 4(3H)- one (II). When (II) was reactedwith 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 aromaticaldehydes furnished 3- [2- (3- benzoyl- 2, 4- diphenyl- 3, 4- dihydro- 2H- [1, 3] oxazino [5, 6-h] quinazolin- 6-yl) ethyl- 2- phenyl- quinazolin -H(3H)- ones (IV). The target compounds (IV) and the intermediates (III) wereevaluated for their antihyperglycemic activity in sucrose loaded rat models.

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