title: Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors.
abstract: Ten azo compounds including azo-resveratrol (5) and azo-oxyresveratrol (9) were synthesized using a modified Curtius rearrangement and diazotization followed by coupling reactions with various phenolic analogs. All synthesized compounds were evaluated for their mushroom tyrosinase inhibitory activity. Compounds 4 and 5 exhibited high tyrosinase inhibitory activity (56.25% and 72.75% at 50 μM, respectively). The results of mushroom tyrosinase inhibition assays indicate that the 4-hydroxyphenyl moiety is essential for high inhibition and that 3,5-dihydroxyphenyl and 3,5-dimethoxyphenyl derivatives are better for tyrosinase inhibition than 2,5-dimethoxyphenyl derivatives. Particularly, introduction of hydroxyl or methoxy group into the 4-hydroxyphenyl moiety diminished or significantly reduced mushroom tryosinase inhibition. Among the synthesized azo compounds, azo-resveratrol (5) showed the most potent mushroom tyrosinase inhibition with an IC(50) value of IC(50)=36.28 ± 0.72 μM, comparable to that of resveratrol, a well-known tyrosinase inhibitor.
authors.affiliation: Molecular Inflammation Research Center for Aging Intervention, College of Pharmacy, Pusan National University, Busan 609-735, Republic of Korea.
authors.forename: Yu Min
authors.initials: YM
authors.lastname: Song
authors.forename: Young Mi
authors.initials: YM
authors.lastname: Ha
authors.forename: Jin-Ah
authors.initials: JA
authors.lastname: Kim
authors.forename: Ki Wung
authors.initials: KW
authors.lastname: Chung
authors.forename: Yohei
authors.initials: Y
authors.lastname: Uehara
authors.forename: Kyung Jin
authors.initials: KJ
authors.lastname: Lee
authors.forename: Pusoon
authors.initials: P
authors.lastname: Chun
authors.forename: Youngjoo
authors.initials: Y
authors.lastname: Byun
authors.forename: Hae Young
authors.initials: HY
authors.lastname: Chung
authors.forename: Hyung Ryong
authors.initials: HR
authors.lastname: Moon
mesh_terms: D000363:Agaricales / Q000201:enzymology; D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010936:Plant Extracts / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000077185:Resveratrol; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D001391:Azo Compounds; D004791:Enzyme Inhibitors; D010936:Plant Extracts; D013267:Stilbenes; C034912:puag-haad; D014442:Monophenol Monooxygenase; D000077185:Resveratrol