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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 6: 1735 - 1746

DOI: https://doi.org/10.6023/cjoc202110004

ARTICLES

Design, Synthesis and Cardioprotection of Cryptotanshinone Derivatives

  • Fangfeng Meng ,
  • Jiahui Zhou ,
  • Xintao Cheng ,
  • Jiahui Xu ,
  • Lei Kang ,
  • Die Li ,
  • Donghao Wang ,
  • Yuefeng Bi
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  • a School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
    b Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, Zhengzhou 450001
† These authors contributed equally to this work
*E-mail:

Received date: 2021-10-03

  Revised date: 2021-12-27

  Online published: 2022-03-03

Supported by

Natural Science Foundation of Henan Province(182300410348)

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Abstract

Cryptotanshinone (CT) is the major lipid-soluble component of Salvia miltiorrhiza, which has myocardial protection and antioxidant effects. To improve its polarity, activity and targets, CT was hybridized with salvianolic acids, the water-soluble active component in salvia miltiorrhiza, and its analogues at its 1 site. A total of 42 derivatives were synthesized, all of which are new compounds. Compared with CT, the polarities of the derivatives were improved. The cardioprotective effects of derivatives were preliminarily evaluated by hypoxia/reoxygenation injury (HRI) model in vitro. The results showed that the activities of most derivatives were enhanced compared with CT, and 6 compounds showed significant effects. Sirtuin 1 (SIRT1) high-throughput activity screening platform and molecular docking technology were used to explore the possible mechanism preliminarily. Structure-activity relationship studies showed that the product activity of 1-position R configuration was better than that of S-configuration, and the activity of aromatic acid derivatives with electron-donating substituents was better than that of with electron-absorbing substituents.

Key words： cryptotanshinone; aromatic acid; hybridization; myocardial protection

Cite this article

Fangfeng Meng , Jiahui Zhou , Xintao Cheng , Jiahui Xu , Lei Kang , Die Li , Donghao Wang , Yuefeng Bi . Design, Synthesis and Cardioprotection of Cryptotanshinone Derivatives[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1735 -1746 . DOI: 10.6023/cjoc202110004

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