1. Academic Validation
  2. Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors

Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors

  • Bioorg Med Chem Lett. 2012 Dec 15;22(24):7451-5. doi: 10.1016/j.bmcl.2012.10.050.
Yu Min Song 1 Young Mi Ha Jin-Ah Kim Ki Wung Chung Yohei Uehara Kyung Jin Lee Pusoon Chun Youngjoo Byun Hae Young Chung Hyung Ryong Moon
Affiliations

Affiliation

  • 1 Molecular Inflammation Research Center for Aging Intervention, College of Pharmacy, Pusan National University, Busan 609-735, Republic of Korea.
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.

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