A partial synthesis of 23-hydroxybetulonic acid and 23-hydroxybetulinic acid starting from betulinic acid

被引：6
|
作者：
Sun, Fei [1 ]
Zhu, Peiqing [1 ]
Yao, Hequan [1 ]
Wu, Xiaoming [1 ]
Xu, Jinyi [1 ]
机构：
[1] China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China
来源：
JOURNAL OF CHEMICAL RESEARCH | 2012年 / 05期
关键词：
betulinic acid; 23-hydroxybetulonic acid; 23-hydroxybetulinic acid; cyclopalladation; Baldwin's method; ANTITUMOR-ACTIVITY; METHYL-GROUPS; CYCLOPALLADATION; DERIVATIVES;
D O I：
10.3184/174751912X13332875186150
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A partial syntheses of the biologically active 23-hydroxybetulonic acid and 23-hydroxybetulinic acid starting from the naturally abundant betulinic acid has been developed in which the key step was the Baldwin's cyclopalladation of the 23-methyl group from a 3-one oxime of betulinic acid, an important drug in Chinese medicine.
引用
收藏
页码：254 / 257
页数：4
相关论文
共 50 条
  • [1] Synthesis and antitumor activity of derivatives of 23-hydroxybetulinic acid
    Jin Pei Zhou~(a
    Chinese Chemical Letters, 2007, (10) : 1195 - 1198
  • [2] Synthesis and antitumor activity of derivatives of 23-hydroxybetulinic acid
    Zhou, Jin Pei
    Li, Dan
    Wu, Xiao Ming
    Ye, Wen Cai
    Zhang, Lu Yong
    CHINESE CHEMICAL LETTERS, 2007, 18 (10) : 1195 - 1198
  • [3] Synthesis and antiproliferative evaluation of 23-hydroxybetulinic acid derivatives
    Lan, Ping
    Wang, Jiao
    Zhang, Dong-Mei
    Shu, Chang
    Cao, Hui-Hui
    Sun, Ping-Hua
    Wu, Xiao-Ming
    Ye, Wen-Cai
    Chen, Wei-Min
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (06) : 2490 - 2502
  • [4] Novel 23-Hydroxybetulinic Acid Derivatives: Semi-Synthesis and Antibacterial Activity
    Xie, Zhongde
    Dai, Xuelian
    Wang, Liqing
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2024, 94 (10) : 2770 - 2788
  • [5] Design, synthesis and antitumor activity of triterpenoid pyrazine derivatives from 23-hydroxybetulinic acid
    Zhang, Hengyuan
    Wang, Yiwei
    Zhu, Peiqing
    Liu, Jie
    Xu, Shengtao
    Yao, Hequan
    Jiang, Jieyun
    Ye, Wencai
    Wu, Xiaoming
    Xu, Jinyi
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 : 235 - 244
  • [6] Effect of 23-hydroxybetulinic acid on lung adenocarcinoma and its mechanism of action
    Tan, Boyu
    Lan, Xiaoxu
    Zhang, Yifan
    Liu, Pai
    Jin, Qiyao
    Wang, Zhiqiang
    Liang, Zhidong
    Song, Wei
    Xuan, Ye
    Sun, Yunxiao
    Li, Youjie
    EXPERIMENTAL AND THERAPEUTIC MEDICINE, 2024, 27 (06)
  • [7] Synthesis, Biological Evaluation of Fluorescent 23-Hydroxybetulinic Acid Probes, and Their Cellular Localization Studies
    Yao, Hong
    Wei, Guoxiang
    Liu, Yanpeng
    Yao, Hequan
    Zhu, Zheying
    Ye, Wencai
    Wu, Xiaoming
    Xu, Jinyi
    Xu, Shengtao
    ACS MEDICINAL CHEMISTRY LETTERS, 2018, 9 (10): : 1030 - 1034
  • [8] Synthesis, biological evaluation and mechanism studies of C-23 modified 23-hydroxybetulinic acid derivatives as anticancer agents
    Lu, Lixue
    Zhang, Hengyuan
    Liu, Jie
    Liu, Yang
    Wang, Yiwei
    Xu, Shengtao
    Zhu, Zheying
    Xu, Jinyi
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 182
  • [9] Synthesis, in vitro and in vivo antitumor activity of pyrazole-fused 23-hydroxybetulinic acid derivatives
    Zhang, Hengyuan
    Zhu, Peiqing
    Liu, Jie
    Lin, Yan
    Yao, Hequan
    Jiang, Jieyun
    Ye, Wencai
    Wu, Xiaoming
    Xu, Jinyi
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (03) : 728 - 732
  • [10] Cytotoxicity of the compounds isolated from Pulsatilla chinensis saponins and apoptosis induced by 23-hydroxybetulinic acid
    Liu, Ming
    Zhao, Xingzeng
    Xiao, Lin
    Liu, Ge
    Liu, Haizhou
    Wang, Xiangyun
    Feng, Xu
    Lin, Xiukun
    PHARMACEUTICAL BIOLOGY, 2015, 53 (01) : 1 - 9
12345