Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors
- Authors
- Song, Yu Min; Ha, Young Mi; Kim, Jin-Ah; Chung, Ki Wung; Uehara, Yohei; Lee, Kyung Jin; Chun, Pusoon; Byun, Youngjoo; Chung, Hae Young; Moon, Hyung Ryong
- Issue Date
- 15-12월-2012
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- Azo-resveratrol; Azo-oxyresveratrol; Curtius rearrangement; Anti-tyrosinase effect; Diazotization
- Citation
- BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, v.22, no.24, pp.7451 - 7455
- Indexed
- SCIE
SCOPUS
- Journal Title
- BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
- Volume
- 22
- Number
- 24
- Start Page
- 7451
- End Page
- 7455
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/106655
- DOI
- 10.1016/j.bmcl.2012.10.050
- ISSN
- 0960-894X
- 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 mu M, 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 mu M, comparable to that of resveratrol, a well-known tyrosinase inhibitor. (C) 2012 Elsevier Ltd. All rights reserved.
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