Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase.
Oxyresveratrol and resveratrol, with hydroxy substituted trans-stilbene structure, exert potent inhibitory effects on cyclooxygenase, rat liver mitochondrial ATPase activity, and tyrosinase. As the isosteres of oxyresveratrol, a new family of hydroxyl substituted phenyl-naphthalenes were synthesized to show excellent inhibition of mushroom tyrosinase. Compound 10, which is isostere of resveratrol, showed IC50 value of 16.52 microM in mushroom tyrosinase activity. As compared to this, the reference compound, resveratrol, showed IC50 value of 55.61 microM. Compound 4, which is isostere of oxyresveratrol, showed IC50 value of 0.49 microM. Among the other three derivatives, compound 13 showed IC50 value of 0.034 microM.
Song
Suhee
S
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea.
Lee
Hyojin
H
Jin
Youngeup
Y
Ha
Young Mi
YM
Bae
Sungjin
S
Chung
Hae Young
HY
Suh
Hongsuk
H
D000363:Agaricales / Q000201:enzymology; D018360:Crystallography, X-Ray; D003640:Dealkylation; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D006873:Hydroquinones / Q000037:antagonists & inhibitors; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D031625:Morus / Q000737:chemistry; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D011753:Pyrones / Q000037:antagonists & inhibitors; D000077185:Resveratrol; D013267:Stilbenes / Q000037:antagonists & inhibitors / Q000737:chemistry
D004791:Enzyme Inhibitors; D006873:Hydroquinones; D007202:Indicators and Reagents; D009281:Naphthalenes; D011753:Pyrones; D013267:Stilbenes; C011890:kojic acid; D014442:Monophenol Monooxygenase; D000077185:Resveratrol; C031927:hydroquinone