Synthesis and antiviral activity of C-3(C-28)-substituted 2,3-seco-triterpenoids

被引:5
作者
Tolmacheva, I. A. [1 ]
Igosheva, E. V. [1 ]
Savinova, O. V. [2 ]
Boreko, E. I. [2 ]
Grishko, V. V. [1 ]
机构
[1] Russian Acad Sci, Inst Tech Chem, Ural Branch, Perm 614013, Russia
[2] Minist Hlth Republ Belarus, RSPC Epidemiol & Microbiol, Minsk 220114, BELARUS
关键词
A-seco-triterpenoids; betulin; betulonic acid; allobetulone; beta-amino alcohols; amides; esters; herpes simplex virus type 1 (HSV-1); ANTI-AIDS AGENTS; BIOLOGICAL-ACTIVITY; ACID-DERIVATIVES; BETULINIC ACID; AMIDES; LUPANE;
D O I
10.1007/s10600-014-0821-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Amide conjugates with four structural types of beta-amino alcohols were synthesized from 2,3-seco-18 alpha H-oleananoic and 2,3-seco-lupane C-3(C-28) mono- and dicarboxylic acids. Esters were prepared by reaction of C-3-hydroxy derivatives of A-seco-triterpenoids with dicarboxylic acid anhydrides. The antiviral activity of the synthesized compounds was studied against herpes simplex virus type I. The most active amide was 5a (5.7 mu M, MTC/EC50 32.2).
引用
收藏
页码:1050 / 1058
页数:9
相关论文
共 50 条
  • [1] Synthesis and antiviral activity of C-3(C-28)-substituted 2,3-seco-triterpenoids
    I. A. Tolmacheva
    E. V. Igosheva
    O. V. Savinova
    E. I. Boreko
    V. V. Grishko
    Chemistry of Natural Compounds, 2014, 49 : 1050 - 1058
  • [2] The immunotropic activity of lupane and oleanane 2,3-seco-triterpenoids
    L. V. Anikina
    I. A. Tolmacheva
    Yu. B. Vikharev
    V. V. Grishko
    Russian Journal of Bioorganic Chemistry, 2010, 36 : 240 - 244
  • [3] The immunotropic activity of lupane and oleanane 2,3-seco-triterpenoids
    Anikina, L. V.
    Tolmacheva, I. A.
    Vikharev, Yu. B.
    Grishko, V. V.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2010, 36 (02) : 240 - 244
  • [4] Synthesis of cytotoxically active derivatives based on alkylated 2,3-seco-triterpenoids
    Konysheva, Anastasia V.
    Nebogatikov, Vladimir.
    Tolmacheva, Irina A.
    Dmitriev, Maxim V.
    Grishko, Victoria V.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 140 : 74 - 83
  • [5] Inhibitors of HIV-1 maturation: Development of structure-activity relationship for C-28 amides based on C-3 benzoic acid-modified triterpenoids
    Swidorski, Jacob J.
    Liu, Zheng
    Sit, Sing-Yuen
    Chen, Jie
    Chen, Yan
    Sin, Ny
    Venables, Brian L.
    Parker, Dawn D.
    Nowicka-Sans, Beata
    Terry, Brian J.
    Protack, Tricia
    Rahematpura, Sandhya
    Hanumegowda, Umesh
    Jenkins, Susan
    Krystal, Mark
    Dicker, Ira B.
    Meanwell, Nicholas A.
    Regueiro-Ren, Alicia
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (08) : 1925 - 1930
  • [6] Synthesis, evaluation of cytotoxicity, and antimicrobial activity of A-azepano- and A-seco-3-amino-C28-aminolupanes
    Kazakova, Oxana B.
    Lopatina, Tatyana V.
    Baikova, Irina P.
    Zileeva, Zulfia R.
    Vakhitova, Yulia V.
    Suponitsky, Kyrill Yu.
    MEDICINAL CHEMISTRY RESEARCH, 2020, 29 (08) : 1507 - 1519
  • [7] Synthesis, evaluation of cytotoxicity, and antimicrobial activity of A-azepano- and A-seco-3-amino-C28-aminolupanes
    Oxana B. Kazakova
    Tatyana V. Lopatina
    Irina P. Baikova
    Zulfia R. Zileeva
    Yulia V. Vakhitova
    Kyrill Yu. Suponitsky
    Medicinal Chemistry Research, 2020, 29 : 1507 - 1519
  • [8] Synthesis and biological activity of amides of 28-methoxy-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oic acid
    E. V. Igosheva
    I. A. Tolmacheva
    Yu. B. Vikharev
    V. V. Grishko
    O. V. Savinova
    E. I. Boreko
    V. F. Eremin
    Chemistry of Natural Compounds, 2012, 48 : 426 - 431
  • [9] Synthesis and biological activity of amides of 28-methoxy-28-oxo-1-cyano-2,3-seco-lup-20(29)-en-3-oic acid
    Igosheva, E. V.
    Tolmacheva, I. A.
    Vikharev, Yu. B.
    Grishko, V. V.
    Savinova, O. V.
    Boreko, E. I.
    Eremin, V. F.
    CHEMISTRY OF NATURAL COMPOUNDS, 2012, 48 (03) : 426 - 431
  • [10] Synthesis and alpha - inhibitory activity of lupane type C2-benzylidene- triterpenoids
    Khusnutdinova, Elmira F.
    Nguyen Thi Thu Ha
    Giniyatullina, Gulnara, V
    Le Thi Tu Anh
    Poptsov, Alexander, I
    Kazakova, Oxana B.
    VIETNAM JOURNAL OF CHEMISTRY, 2021, 59 (05) : 612 - 619