Journal of Chemical and Pharmaceutical Research (ISSN : 0975-7384)

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Original Articles: 2011 Vol: 3 Issue: 5

Synthesis of new b -D-glucuronides: b -D-glucuronosyl-5- (3-aryl-1H-pyrazol- 5-yl)-1,2-benzisoxazole-3-carboxylates


1-(3-Methylbenzo isoxazol-5-yl)-3-phenyl prop-2-en-1-one 1 undergoes interaction with hydrazine hydrate to yield 3-methyl-5-(3-phenyl-1H-pyrazol-5-yl)-1,2-benzisoxazole 2, which on oxidation with KMnO4 gives 5-(3-phenyl-1H-pyrazol-5-yl)-1,2-benzisoxazole-3-carboxylic acid 3. Glucuronidation of these 5-(3-phenyl-1H-pyrazol-5-yl)-1,2- benzisoxazole-3-carboxylic acid 3 with free glucuronic acid afforded b -D-glucuronosyl-5-(3-phenyl-1H-pyrazol-5-yl)-1,2- benzisoxazole-3-carboxylate 4. The structures of the products have been assigned on the basis of 1H NMR, 13C NMR, FAB-MS, optical activity, and elemental analysis. The title compounds are found to have antibacterial and antifungal activities.