Sulfation of Allobetulin with Sulfamic Acid in N, N-dimethylformamide and 1,4-dioxane

被引:0
作者
Levdansky, Vladimir A. [1 ]
Ivanenko, Timur Yu. [1 ]
Levdansky, Alexander V. [1 ]
机构
[1] RAS, Inst Chem & Chem Technol, SB, FRC,KSC, Krasnoyarsk, Russia
来源
JOURNAL OF SIBERIAN FEDERAL UNIVERSITY-CHEMISTRY | 2024年 / 17卷 / 03期
关键词
allobetulin; sulfation; sulfamic acid; urea; 1,4-dioxane; N; N-dimethylformamide; 3-sulfate; CYTOTOXICITY; BETULIN;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Sulfuric acid esters of betulin and its numerous derivatives are of interest to the chemical and pharmaceutical industry as complement inhibitors. The development of new efficient methods for the synthesis of sulfuric acid esters of betulin and its derivatives is an actual task. The sulfation of allobetulin with sulfamic acid in the presence of urea in a medium of 1,4-dioxane and N, N-dimethylformamide was studied for the first time. It was found that the reaction proceeds in a homogeneous medium at a temperature of 70-75 degrees C in 3-4 hours with the formation of allobetulin 3-sulfate. The structure of allobetulin 3-sulfate was confirmed by FTIR and NMR spectroscopy, and its composition was confirmed by elemental analysis.
引用
收藏
页码:448 / 456
页数:9
相关论文
共 22 条
  • [1] Selective inhibition of the interaction of C1q with immunoglobulins and the classical pathway of complement activation by steroids and triterpenoids sulfates
    Bureeva, Svetlana
    Andia-Pravdivy, Julian
    Symon, Andrey
    Bichucher, Anna
    Moskaleva, Vera
    Popenko, Vladimir
    Shpak, Alexey
    Shvets, Vitaly
    Kozlov, Leonid
    Kaplun, Alexander
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (10) : 3489 - 3498
  • [2] Allobetulin and Its Derivatives: Synthesis and Biological Activity
    Dehaen, Wim
    Mashentseva, Anastassiya A.
    Seitembetov, Talgat S.
    [J]. MOLECULES, 2011, 16 (03) : 2443 - 2466
  • [3] Gordon A.J., 1972, The Chemist's Companion, P537
  • [4] Synthesis of triterpenoid sulfates using the SO3-dimethyl sulfoxide complex
    Grishkovets, VI
    [J]. CHEMISTRY OF NATURAL COMPOUNDS, 1999, 35 (01) : 73 - 74
  • [5] Simple structural modifications confer cytotoxicity to allobetulin
    Heller, Lucie
    Obernauer, Anja
    Csuk, Rene
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (13) : 3002 - 3012
  • [6] Kaplun A. P., 2004, Publ
  • [7] New reactions of betulin with sulfamic acid and ammonium sulfamate in the presence of solid catalysts
    Kazachenko, Aleksandr S.
    Vasilieva, Natalya Yu
    Fetisova, Olga Yu
    Sychev, Valentine V.
    Elsuf'ev, Evgeniy, V
    Malyar, Yuriy N.
    Issaoui, Noureddine
    Miroshnikova, Angelina, V
    Borovkova, Valentina S.
    Kazachenko, Anna S.
    Berezhnaya, Yaroslava D.
    Skripnikov, Andrey M.
    Zimonin, Dmitry, V
    Ionin, Vladislav A.
    [J]. BIOMASS CONVERSION AND BIOREFINERY, 2024, 14 (03) : 4245 - 4256
  • [8] Synthesis and cytotoxicity of allobetulin derivatives
    Kazakova, O. B.
    Smirnova, I. E.
    Khusnutdinova, E. F.
    Zhukova, O. S.
    Fetisova, L. V.
    Apryshko, G. N.
    Medvedeva, N. I.
    Yamansarov, E. Yu.
    Baikova, I. P.
    Thanh Tra Nguyen
    Thu, H. Do Thi
    [J]. RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2014, 40 (05) : 558 - 567
  • [9] Kislitsyn A. N., 1976, Method of preparing allobetulin
  • [10] Sulfonation of Betulinic Acid by Sulfamic Acid
    Levdanskii, V. A.
    Levdanskii, A. V.
    Kuznetsov, B. N.
    [J]. CHEMISTRY OF NATURAL COMPOUNDS, 2015, 51 (05) : 894 - 896