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

Yu Min Song, Young Mi Ha, Jin Ah Kim, Ki Wung Chung, Yohei Uehara, Kyung Jin Lee, Pusoon Chun, Youngjoo Byun, Hae Young Chung, Hyung Ryong Moon

Research output: Contribution to journalArticlepeer-review

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 IC50 value of IC50 = 36.28 ± 0.72 μM, comparable to that of resveratrol, a well-known tyrosinase inhibitor.

Original languageEnglish (US)
Pages (from-to)7451-7455
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number24
DOIs
StatePublished - Dec 15 2012
Externally publishedYes

Keywords

  • Anti-tyrosinase effect
  • Azo-oxyresveratrol
  • Azo-resveratrol
  • Curtius rearrangement
  • Diazotization

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

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