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

doi:10.6023/cjoc201709021

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

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新型苦参碱衍生物的水相合成及其晶体结构

王伟, 吕梦娇, 赵利霞, 张娅玲, 李本浩, 李宝林

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 E-mail:wwlzz@snnu.edu.cn;baolinli@snnu.edu.cn
基金资助:
国家自然科学基金（No.21272144）和中央高校基本科研业务费专项资金（Nos.1301030054，X2015YB06）资助项目.

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

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

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 E-mail:wwlzz@snnu.edu.cn;baolinli@snnu.edu.cn
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).

1. Synthesis of New Matrine Derivatives in Aqueous Phase and Their Crystal Structures.PDF(1331KB)

Abstract

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

Cite this article

Wang Wei, Lü Mengjiao, Zhao Lixia, Zhang Yaling, Li Benhao, Li Baolin. Synthesis of New Matrine Derivatives in Aqueous Phase and Their Crystal Structures[J]. Chin. J. Org. Chem., 2018, 38(4): 883-889.

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新型苦参碱衍生物的水相合成及其晶体结构

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

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