Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents
Chen, Hao1,2; Ma, Yun-Bao1; Huang, Xiao-Yan1; Geng, Chang-An1; Zhao, Yong1,2; Wang, Li-Jun1; Guo, Rui-Hua1; Liang, Wen-Juan1,2; Zhang, Xue-Mei1; Chen, Ji-Jun1
2014-05-15
发表期刊BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN0960-894X
卷号24期号:10页码:2353-2359
摘要Dehydroandrographolide and andrographolide, two natural diterpenoids isolated from Andrographis paniculata possessed activity against HBV DNA replication with IC50 values of 22.58 and 54.07 mu M and low SI values of 8.7 and 3.7 in our random assay. Consequently, 48 derivatives of dehydroandrographolide and andrographolide were synthesized and evaluated for their anti-HBV properties to yield a series of active derivatives with lower cytotoxicity, including 14 derivatives against HBsAg secretion, 19 derivatives against HBeAg secretion and 38 derivatives against HBV DNA replication. Interestingly, compound 4e could inhibit not only HBsAg and HBeAg secretions but also HBV DNA replication with SI values of 20.3, 125.0 and 104.9. Furthermore, the most active compound 2c with SI value higher than 165.1 inhibiting HBV DNA replication was revealed with the optimal logP value of 1.78 and logD values. Structureactivity relationships (SARs) of the derivatives were disclosed for guiding the future research toward the discovery of new anti-HBV drugs. (C) 2014 Elsevier Ltd. All rights reserved.
关键词Anti-hbv Activity DehydroAndrographolide And Andrographolide Derivatives Structure-activity Relationships Octanol-water Partition Coefficients
资助信息National Natural Science Foundation of China for Distinguished Young Scholars [81025023]; National Natural Science Foundation of China [81202436]; West Light Foundation of the Chinese Academy of Sciences; Youth Innovation Promotion Association, CAS
学科领域Pharmacology & Pharmacy ; Chemistry
DOI10.1016/j.bmcl.2014.03.060
收录类别SCI ; IC
语种英语
WOS研究方向Pharmacology & Pharmacy ; Chemistry
WOS类目Chemistry, Medicinal ; Chemistry, Organic
WOS记录号WOS:000335517300024
引用统计
被引频次:31[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/18112
专题植物化学与西部植物资源持续利用国家重点实验室
作者单位1.Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West C, Kunming Inst Bot, Kunming 650201, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
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Chen, Hao,Ma, Yun-Bao,Huang, Xiao-Yan,et al. Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2014,24(10):2353-2359.
APA Chen, Hao.,Ma, Yun-Bao.,Huang, Xiao-Yan.,Geng, Chang-An.,Zhao, Yong.,...&Chen, Ji-Jun.(2014).Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,24(10),2353-2359.
MLA Chen, Hao,et al."Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 24.10(2014):2353-2359.
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