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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 9: 2764 - 2771

DOI: https://doi.org/10.6023/cjoc202004033

Synthesis and Anticancer Evaluation of Amido-Derivative of Hydnocarpin D

  • Maihesuti Liwaliding ,
  • Yu Junjie ,
  • Wang Qi ,
  • Cao Jianguo ,
  • Huang Guozheng
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  • 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 date: 2020-04-21

  Revised date: 2020-06-10

  Online published: 2020-07-17

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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

Cite this article

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 . DOI: 10.6023/cjoc202004033

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