Synthesis of Cinnamic Acid-Coumarin Ester Analogs and Inhibition of Tyrosinase Activity

doi:10.6023/cjoc202005006

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2980-2987.DOI: 10.6023/cjoc202005006 Previous Articles Next Articles

肉桂酸-香豆素酯类似物的合成及抑制酪氨酸酶活性研究

林芷晴^a, 夏婉铃^a, 刘仁义^a, 姜少华^a, 马志强^a,b

a 五邑大学生物科技与大健康学院广东江门 529000;
b 华南理工大学化学与化工学院广州 510641

收稿日期:2020-05-04 修回日期:2020-05-29 发布日期:2020-06-20
通讯作者: 姜少华, 马志强 E-mail:wyuchemjsh@126.com;23090330@qq.com
基金资助:
广东省教育厅基金（Nos.2017KSYS010，2017KZDXM084，2019KZDZX2003，2019KZDXM035）资助项目.

Synthesis of Cinnamic Acid-Coumarin Ester Analogs and Inhibition of Tyrosinase Activity

Lin Zhiqing^a, Xia Wanling^a, Liu Renyi^a, Jiang Shaohua^a, Ma Zhiqiang^a,b

a School of Biotechnology and Grand Health, Wuyi University, Jiangmen, Guangdong 529000;
b School of Chemistry & Chemical Engineering, South China University of Technology, Guangzhou 510641

Received:2020-05-04 Revised:2020-05-29 Published:2020-06-20
Supported by:
Project supported by the Department of Education of Guangdong Province (Nos. 2017KSYS010, 2017KZDXM084, 2019KZDZX2003, 19KZDXM035).

1. cjoc202005006.pdf(2421KB)

Abstract

In medicinal chemistry, the structural modification of natural product and skeleton hybridization strategies is important way to improve the biological activity of template compound and find highly active lead compounds. In this work, two series of cinnamic acid-coumarin ester analogs were synthesized by using cinnamic acid and hydroxycoumarin as raw materials. And the tyrosinase inhibitory activity of the synthesized compounds was evaluated. The results indicated that the cinnamic acid-coumarin analogs had favourable tyrosinase inhibitory activity, especially 2-oxo-2H-benzopyran-4-yl(E)-3-(4-hydroxyphenyl)propenyl ester (C₈), 2-oxo-2H-benzopyran-7-yl(E)-3-(4-hydroxyphenyl)propenyl ester and (D₈) with IC₅₀ of (10.7±0.7) and (2.2±0.2) μmol·L^-1, respectively, which are 3 and 13 times that of kojic acid (IC₅₀ (28.5±1.1) μmol·L^-1). The structure-activity relationship analysis results showed that the introduction of substituents like F, Cl, and OH could efficiently enhance the tyrosinase inhibitory activity, and the inhibitory activity of condensation product of substituted cinnamic acid with 7-hydroxycoumarin was higher than that of substituted cinnamic acid with 4-hydroxycoumarin. Kinetic studies showed that the inhibitions of tyrosinase by compounds C₈ and D₈ are reversible mixed-type inhibitory effects. K_I values of C₈ and D₈ were 1.07 and 20.61 μmol·L^-1, respectively, and K_IS values were 3.72 and 27.09 μmol·L^-1, respectively. Finally, molecular docking was carried out to simulate the docking between compounds C₈ and D₈ with tyrosinase.

Key words: tyrosinase, coumarin, cinnamic acid, molecular docking

Cite this article

Lin Zhiqing, Xia Wanling, Liu Renyi, Jiang Shaohua, Ma Zhiqiang. Synthesis of Cinnamic Acid-Coumarin Ester Analogs and Inhibition of Tyrosinase Activity[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2980-2987.

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肉桂酸-香豆素酯类似物的合成及抑制酪氨酸酶活性研究

Synthesis of Cinnamic Acid-Coumarin Ester Analogs and Inhibition of Tyrosinase Activity

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