Palladium(II)-Catalyzed Efficient Synthesis of Wedelolactone and Evaluation as Potential Tyrosinase Inhibitor

Molecules

Jianqiu Chen¹  Fei Ji¹  Huidan Huang¹  Chaofeng Zhang²  Jie Ren² 

[1] College of Engineering, China Pharmaceutical University, 639 Longmian Avenue, Jiangning District, Nanjing 211198, China;State Key Laboratory of Natural Medicines, Research Department of Pharmacognosy, China Pharmaceutical University, 639 Longmian Avenue, Jiangning District, Nanjing 211198, China;

关键词: wedelolactone (wel);    tyrosinase;    suzuki–miyaura reaction;    inhibitors;   

DOI  :  10.3390/molecules24224130

来源: DOAJ

【 摘 要 】

Tyrosinase is an enzyme widely distributed in nature, which has multiple functions, especially in the melanin biosynthesis pathway. Despite the few clinically available tyrosinase inhibitors for whitening, a great demand remains for novel compounds with low side effects in terms of potential carcinogenicity and improved clinical efficacy. A natural product, wedelolactone (WEL), with a polyhydroxyl moiety, attracted our attention as a potential tyrosinase inhibitor. Before we studied the biological activity of the natural product, a synthetic methodological research was firstly carried to obtain enough raw material. WEL could be obtained efficiently through palladium-catalyzed boronation/coupling reactions and 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ)-involved oxidative deprotection/annulation reactions. Immediately after, the natural product was proven to be an efficient tyrosinase inhibitor. In conclusion, we developed a mild and efficient approach for the preparation of WEL, and the natural product was disclosed to have anti-tyrosinase activity, which could be widely used in multiple fields.

【 授权许可】

Unknown