Synthesis, Structure Activity Relationship and Anti-influenza A Virus Evaluation of Oleanolic Acid-Linear Amino Derivatives

被引：18
|
作者：
Li, Weijia [1 ]
Yang, Fan [1 ]
Meng, Lingkuan [1 ]
Sun, Jiaqi [2 ]
Su, Yangqing [1 ]
Shao, Liang [1 ]
Zhou, Demin [2 ]
Yu, Fei [1 ]
机构：
[1] Kunming Univ Sci & Technol, Med Sch, Kunming 650500, Yunnan, Peoples R China
[2] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 2019年 / 67卷 / 11期
基金：
中国国家自然科学基金;
关键词：
oleanolic acid; influenza virus; entry inhibitor; cytotoxicity; synthesis design; INFLUENZA;
D O I：
10.1248/cpb.c19-00485
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Oleanolic acid (OA) was discovered as a mild influenza hemagglutinin (HA) inhibitor in our earlier studies. In the present work, 20 compounds were prepared by structural modifications of OA, and their antiviral activities against influenza A/WSN/33 (H1N1) virus in Madin-Darby canine kidney (MDCK) cells were evaluated. Based on the biological result, structure activity relationship (SAR) was discussed. Compound 10 with six-carbon chain and a terminal hydroxyl group showed the strongest anti-influenza activity with an IC50 of 2.98 mu M, which is an order of magnitude more potent than OA. Hemagglutination inhibition and Surface plasmon resonance (SPR) assay indicated that compound 10 might interfere with influenza invasion by interacting with HA protein.
引用
收藏
页码：1201 / 1207
页数：7
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