Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
10594192 | Bioorganic & Medicinal Chemistry Letters | 2012 | 5 Pages |
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.
Keywords
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
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,