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 mu M in mushroom tyrosinase activity. As compared to this, the reference compound, resveratrol, showed IC50 value of 55.61 mu M. Compound 4, which is isostere of oxyresveratrol, showed IC50 value of 0.49 mu M. Among the other three derivatives, compound 13 showed IC50 value of 0.034 mu M. (c) 2006 Elsevier Ltd. All rights reserved.