Synthesis and Anticancer Evaluation of Amido-Derivative of Hydnocarpin D

doi:10.6023/cjoc202004033

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2764-2771.DOI: 10.6023/cjoc202004033 Previous Articles Next Articles

次大风子素酰胺类衍生物的合成及抗癌活性评价

力瓦衣丁·买合苏提^a,c, 於俊杰^b, 王琪^b, 曹建国^b, 黄国正^a,b

a 中国科学院新疆理化技术研究所干旱区植物资源与化学重点实验室乌鲁木齐 830011;
b 上海师范大学生命科学学院上海 201418;
c 中国科学院大学北京 100049

收稿日期:2020-04-21 修回日期:2020-06-10 发布日期:2020-07-17
通讯作者: 黄国正, 曹建国 E-mail:guozheng.huang@yahoo.com;cao101@shnu.edu.cn

Synthesis and Anticancer Evaluation of Amido-Derivative of Hydnocarpin D

Maihesuti Liwaliding^a,c, Yu Junjie^b, Wang Qi^b, Cao Jianguo^b, Huang Guozheng^a,b

a Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011;
b College of Life Sciences, Shanghai Normal University, Shanghai 201418;
c University of Chinese Academy of Sciences, Beijing 100049

Received:2020-04-21 Revised:2020-06-10 Published:2020-07-17

1. cjoc202004033.pdf(1327KB)

Abstract

Hydnocarpins are a rare type of flavonoligan compounds occurring in nature. Because of their rarity, only a few research has been devoted on their structural modification and activity. In this work, 23-iodo hydnocarpin D was synthesized from silibinin, which is cheap and commericially available. After azidation, reduction and amidation, 15 amido-derivatives of hydnocarpin D were obtained. These compounds with regard to their anticancer activities were evaluated on three kinds of human cancer cells, and the results showed that some compounds are active on A549 with IC₅₀ values less than 10 μmol·L^-1. 23-(3,4-Dimethoxybenzamido)hydnocarpin D (6b) and 23-(2-chloro-4-fluorobenzamido)hydnocarpin D (6f) can strongly inhibit the growth of HeLa cells. 23-(4-Fluorobenzamido)hydnocarpin D (6g) and 23-[3,5-bis(trifluoromethyl)benzamido]-hydnocarpin D (6m) showed potent activity against MCF-7 cells. These preliminary results testified that the synthsis of amido-derivative of hydnocarpin D could be an option for the development of new anti-cancer drug candidates.

Key words: hydnocarpin D, silibinin, structural modification, anticancer activity

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Maihesuti Liwaliding, Yu Junjie, Wang Qi, Cao Jianguo, Huang Guozheng. Synthesis and Anticancer Evaluation of Amido-Derivative of Hydnocarpin D[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2764-2771.

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次大风子素酰胺类衍生物的合成及抗癌活性评价

Synthesis and Anticancer Evaluation of Amido-Derivative of Hydnocarpin D

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