SYNTHESIS, POLAROGRAPHIC AND ANTIMICROBIAL STUDIES OF BENZISOXAZOLYLN- GLUCOSIDES

Abstract

The desired compounds 7-amino-3-methyl-5-(3′-aryl prop-2′-enoyl)-1,2-benzisoxazoles 2a-j were prepared by the reaction of appropriate 5-acetyl-7-amino-3-methyl-1,2-benzisoxazole 1 with different aromatic aldehydes. The reaction of (2a-j) with hydroxylamine hydrochloride was done to form 7-amino-3-methyl-5-(3′-aryl isoxazol-5′-yl)-1,2- benzisoxazoles (3a-j). Condensation of tetra-O-acetyl-α-D-glucopyranosyl bromide (TAGBr) with 7-amino-3-methyl-5- (3′-aryl isoxazol-5′-yl)-1,2-benzisoxazoles furnishes 7-amino-(β-D-2,3,4,6-tetra-O-acetyl glucopyranosyl)-3-methyl-5- (3′-aryl isoxazol-5′-yl)-1,2-benzisoxazoles (4a-j) which on deprotection yielded 7-amino-(β-D-glucopyranosyl)-3- methyl-5-(3′-aryl isoxazol-5′-yl)-1,2-benzisoxazoles (5a-j). The identities of newly synthesized compounds were established on the basis of IR, 1HNMR, 13CNMR, Mass spectral, Elemental analysis, TLC, and Polarographic studies. All compounds have been evaluated for antimicrobial activities and some compounds show potent activities.