Synthesis and Anti-inflammatory Activity Evaluation of 2-Dehydroepiandrosterone Benzene Methyl Derivatives

doi:10.6023/cjoc201901039

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2625-2631.DOI: 10.6023/cjoc201901039 Previous Articles Next Articles

ARTICLE

2-去氢表雄酮苯亚甲基衍生物的合成及抗炎活性研究

朱丽^a,b, 杨艳秋^c, 高佩佩^a,b, 安雪^a,b, 孙莹莹^a,b, 孙晓雯^a,b, 侯悦^c, 单丽红^a,b

a 郑州大学药学院郑州 450001;
b 新药创制与药物安全性评价河南省协同创新中心郑州 450001;
c 东北大学生命科学与健康学院沈阳 110819

收稿日期:2019-01-25 修回日期:2019-03-22 发布日期:2019-04-11
通讯作者: 侯悦, 单丽红 E-mail:shlh@zzu.edu.cn;houyue@mail.neu.edu.cn
基金资助:
国家自然科学基金（Nos.21402178，U1603125）和河南省科学研究基金（No.132300410195）资助项目.

Synthesis and Anti-inflammatory Activity Evaluation of 2-Dehydroepiandrosterone Benzene Methyl Derivatives

Zhu Li^a,b, Yang Yanqiu^c, Gao Peipei^a,b, An Xue^a,b, Sun Yingying^a,b, Sun Xiaowen^a,b, Hou Yue^c, Shan Lihong^a,b

a School of Pharmaceutical Sciences, Zhengzhou 450001;
b Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou 450001;
c College of Life and Health Sciences, Northeastern University, Shenyang 110819

Received:2019-01-25 Revised:2019-03-22 Published:2019-04-11
Contact: 10.6023/cjoc201901039 E-mail:shlh@zzu.edu.cn;houyue@mail.neu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21402178, U1603125) and the Scientific Research Fund of Henan Province (No. 132300410195).

1. Synthesis and Anti-inflammatory Activity Evaluation of 2-Dehydroepiandrosterone Benzene Methyl Derivatives.PDF(1693KB)

Abstract

Alzheimer's Disease (AD) is one of the major health crises in the 21st century, and due to the complexity of its pathogenesis, there has no good solution to cure this disease. In order to find more economical and effective drugs for the treatment of neurodegenerative diseases, a series of novel 2-dehydroepiandrosterone benzathine derivatives were synthesized and their activity on the NO release of microglia cell line BV-2 activated by lipopolysaccharide (LPS), as well as their effect on cell viability were studied. The structures of the synthesized compounds were confirmed by ¹H NMR, ¹³C NMR and HRMS. The results showed that all compounds had inhibitory effects on the NO release of LPS-activated mouse microglial cell line BV2 after 24 h of treatment, and it was dose-dependent. In particular, the IC₅₀ values of 2-(3-chloro)benzylidene-15β,16β-methylene-androstane-4,6-diene-3,17-dione (5a) and 2-(3,4,5-trimethoxy)benzylidene-15β,16β-methylene-androstane-4,6-die-ne-3,17-dione (5j) were 2.69 and 3.28 μmol·L^-1, respectively, which were better than the positive control Minocycline. The results showed that these compounds may be effective in the development of neurodegenerative diseases involving activation of microglia, and the mechanism deserved further study.

Key words: dehydroepiandrosterone, chalcone analogue, alzheimer's disease, microglia

Cite this article

Zhu Li, Yang Yanqiu, Gao Peipei, An Xue, Sun Yingying, Sun Xiaowen, Hou Yue, Shan Lihong. Synthesis and Anti-inflammatory Activity Evaluation of 2-Dehydroepiandrosterone Benzene Methyl Derivatives[J]. Chin. J. Org. Chem., 2019, 39(9): 2625-2631.

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2-去氢表雄酮苯亚甲基衍生物的合成及抗炎活性研究

Synthesis and Anti-inflammatory Activity Evaluation of 2-Dehydroepiandrosterone Benzene Methyl Derivatives

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