Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (4): 883-889.DOI: 10.6023/cjoc201709021 Previous Articles     Next Articles



王伟, 吕梦娇, 赵利霞, 张娅玲, 李本浩, 李宝林   

  1. 陕西师范大学化学化工学院 教育部药用资源与天然药物化学重点实验室 西安 710062
  • 收稿日期:2017-09-13 修回日期:2017-10-11 发布日期:2017-12-05
  • 通讯作者: 王伟, 李宝林;
  • 基金资助:


Synthesis of New Matrine Derivatives in Aqueous Phase and Their Crystal Structures

Wang Wei, Lü Mengjiao, Zhao Lixia, Zhang Yaling, Li Benhao, Li Baolin   

  1. Key Laboratory of Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710062
  • Received:2017-09-13 Revised:2017-10-11 Published:2017-12-05
  • Contact: 10.6023/cjoc201709021;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272144) and the Fundamental Research Funds for the Central Universities (Nos. 1301030054, X2015YB06).

Thirteen matrine derivatives were synthesized with high yield with one step in aqueous phase. The chemical structures of the synthesized compounds were characterized by 1H NMR, 13C NMR and HRMS. Three crystals of compound 13-(piperidin-1-yl)matrine (a), 13-(piperidin-1-yl)carbodithioate matrine (k) and 13-(morpholin-4-yl) carbodithioate matrine (m) were obtained and X-ray diffraction data showed that their structures included five chiral carbon atoms with the absolute configuration of 5(S), 6(S), 7(R), 11(R) and 13(S). Meanwhile, there were three classical hydrogen bonds:O(2)-H(21B)…N(2), O(2)-H(21A)…O(1) and C(9)-H(9A)…O(1) by analyzing the data of compound 13-(piperidin-1-yl) matrine (a). These strong hydrogen bonds can play a key role in the accumulation of crystals. Biological studies indicated that the synthetic derivatives had some inhibitory effect against SW480, A549 and A431 cells. The introduction of N or S atom at C-13 position of matrine could improve the antitumor activity.

Key words: matrine, derivative, synthesis, crystal