1-1-diphenyl-2-picrylhydrazyl and 5-7-dihydroxy-6-methoxy-2-phenylchromen-4-one

Pharmacologically motivated natural product investigations have yielded a large variety of structurally unique lead compounds with interesting biomedical properties, but the natural roles of these molecules often remain unknown. In the present investigation, a series of benzyl substituted-flavone derivatives have been synthesized from the lead compounds and were screened against 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging and α-glucosidase inhibitory properties. The resulting activity profiles of these flavone derivatives were compared for degree of similarity to the profile of 1-3. Most of the synthesized derivatives displayed potent activities when compared to the parent compounds. Maximum potencies for DPPH free radical scavenging activity were observed only in compounds containing the 4-hydroxyl substitution and 3-methoxyl group on the phenyl ring. While the 2- and 4-hydroxyl group substitutions on the phenyl ring seem to be crucial for the intestinal α-glucosidase inhibitory activity.

Topics: Benzene Derivatives; Bignoniaceae; Biphenyl Compounds; Flavanones; Flavonoids; Free Radical Scavengers; Glycoside Hydrolase Inhibitors; Hypoglycemic Agents; India; Molecular Structure; Picrates; Plant Roots; Plants, Medicinal