Synthesis and biological evaluation of novel 4-hydroxybenzaldehyde derivatives as tyrosinase inhibitors

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• 作者：Wei Yi ; Rihui Cao ; Wenlie Peng ; Huan Wen ; Qin Yan ; Binhua Zhou ; Lin Ma ; Huacan Song
• 关键词：Synthesis ; 4-Hydroxybenzaldehyde derivatives ; Tyrosinase inhibitors ; Inhibition mechanism ; Acute toxicity
• 刊名：European Journal of Medicinal Chemistry
• 出版年：2010
• 出版时间：February 2010
• 年：2010
• 卷：45
• 期：2
• 页码：639-646
• 全文大小：371 K

文摘

A series of novel 4-hydroxybenzaldehyde derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were investigated. Most of target compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC₅₀ = 1.22 mM). Interestingly, compound 3c bearing a dimethoxyl phosphate was found to be the most potent inhibitor with IC₅₀ value of 0.059 mM. The inhibition kinetics analyzed by Lineweaver–Burk plots revealed that compound 3c was a non-competitive inhibitor (K_I = 0.0368 mM). In particular, compound 3c showed no side effects at dose of 1600 mg/kg in mice. These results suggested that such compounds might be served as lead compounds for further designing new potential tyrosinase inhibitors.