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
  • [21] Synthesis, biological evaluation and mechanism studies of C-3 substituted nitrogenous heterocyclic 23-Hydroxybetulinic acid derivatives as anticancer agents
    Zhou, Haipin
    Zhu, Huajian
    Zha, Yuxin
    Xu, Jinyi
    Wang, Tingfang
    Xu, Shengtao
    FITOTERAPIA, 2022, 160
  • [22] Bipiperidinyl derivatives of 23-hydroxybetulinic acid reverse resistance of HepG2/ADM and MCF-7/ADR cells
    Zhang, Dong-Mei
    Li, Ying-Jie
    Shu, Chang
    Ruan, Zhi-Xiong
    Chen, Wei-Min
    Yiu, Anita
    Peng, Ying-Hui
    Wang, Jiao
    Lan, Ping
    Yao, Zhe
    Fung, Kwok-Pui
    Fu, Li-Wu
    Chen, Zhe-Sheng
    Ye, Wen-Cai
    ANTI-CANCER DRUGS, 2013, 24 (05) : 441 - 454
  • [23] Apoptotic activity of 23 - Hydroxybetulinic acid on Lovo cell line
    Yan, Cheng
    Wencai, Ye
    Hiroshi, Kurihara
    Xinsheng, Yao
    ACTA PHARMACOLOGICA SINICA, 2006, 27 : 69 - 69
  • [24] 23-HYDROXYBETULINIC ACID ENHANCES THE CYTOTOXICITY OF CHEMOTHERAPEUTIC AGENTS THROUGH MODULATING P-GLYCOPROTEIN-MEDIATED RESISTANCE IN VITRO
    Zheng, Yuanting
    Wu, Xiaolan
    Wang, Guangji
    Hao, Haiping
    Zhou, Fang
    Sun, Jianguo
    Gu, Yi
    Yan, Bei
    Li, Yannan
    DRUG METABOLISM REVIEWS, 2008, 40 : 191 - 192
  • [25] Design and synthesis of NAD(P)H: Quinone oxidoreductase (NQO1)-activated prodrugs of 23-hydroxybetulinic acid with enhanced antitumor properties
    Zhu, Huajian
    Lu, Lixue
    Zhu, Wenjian
    Tan, Yuchen
    Duan, Yiping
    Liu, Jie
    Ye, Wencai
    Zhu, Zheying
    Xu, Jinyi
    Xu, Shengtao
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2022, 240
  • [26] Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives
    Zhang, Hengyuan
    Zhu, Peiqing
    Liu, Jie
    Yang, Xue
    Xu, Shengtao
    Yao, Hequan
    Jiang, Jieyun
    Ye, Wencai
    Wu, Xiaoming
    Xu, Jinyi
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 87 : 159 - 167
  • [27] TERPENOIDS .23. INTERCONVERSION OF THURBEROGENIN AND BETULINIC ACID
    DJERASSI, C
    HODGES, R
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (14) : 3534 - 3538
  • [28] Protective effect of 23-hydroxybetulinic acid on doxorubicin-induced cardiotoxicity: a correlation with the inhibition of carbonyl reductase-mediated metabolism
    Zhou, Fang
    Hao, Gang
    Zhang, Jingwei
    Zheng, Yuanting
    Wu, Xiaolan
    Hao, Kun
    Niu, Fang
    Luo, Dan
    Sun, Yuan
    Wu, Liang
    Ye, Wencai
    Wang, Guangji
    BRITISH JOURNAL OF PHARMACOLOGY, 2015, 172 (23) : 5690 - 5703
  • [29] 23-hydroxybetulinic acid reduces tumorigenesis, metastasis and immunosuppression in a mouse model of hepatocellular carcinoma via disruption of the MAPK signaling pathway
    Tian, Dazhi
    Yu, Yang
    Zhang, Li
    Sun, Jisan
    Jiang, Wentao
    ANTI-CANCER DRUGS, 2022, 33 (09) : 815 - 825
  • [30] 23-Hydroxybetulinic acid-mediated apoptosis is accompanied by decreases in bcl-2 expression and telomerase activity in HL-60 Cells
    Ji, ZN
    Ye, WC
    Liu, GG
    Hsiao, WLW
    LIFE SCIENCES, 2002, 72 (01) : 1 - 9
12345