Synthesis and biological evaluation of novel benzyl-substituted flavones as free radical (DPPH) scavengers and α-glucosidase inhibitors.
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.
Division of Organic Chemistry-I, Natural Product Laboratory, Indian Institute of Chemical Technology, Hyderabad, India.
G Suresh
GS
Kumar
Ashok K
AK
Tiwari
V Rama Subba
VR
Rao
K Rajendra
KR
Prasad
A Zehra
AZ
Ali
K Suresh
KS
Babu
D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D029402:Bignoniaceae / Q000737:chemistry; D001713:Biphenyl Compounds / Q000494:pharmacology; D044950:Flavanones; D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007194:India; D015394:Molecular Structure; D010851:Picrates / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry
D001555:Benzene Derivatives; D001713:Biphenyl Compounds; D044950:Flavanones; D005419:Flavonoids; D016166:Free Radical Scavengers; D065089:Glycoside Hydrolase Inhibitors; D007004:Hypoglycemic Agents; D010851:Picrates; C043561:chrysin; C006680:baicalein; C080669:5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one; C004931:1,1-diphenyl-2-picrylhydrazyl