Synthesis and Intramolecular Cyclization of a 2,3-seco-Oleanane Triterpenoid with an Ethylketone Fragment

被引：5
|
作者：
Konysheva, A. V. [1 ]
Zhukova, A. E. [1 ]
Dmitriev, M. V. [2 ]
Grishko, V. V. [1 ]
机构：
[1] Russian Acad Sci, Inst Tech Chem, Ural Branch, Perm 614013, Russia
[2] Perm State Natl Res Univ, Perm 614990, Russia
来源：
CHEMISTRY OF NATURAL COMPOUNDS | 2018年 / 54卷 / 06期
关键词：
triterpenoids; allobetulone; Grignard reaction; nitrile-anionic cyclization; oxo-nitrile cyclization; cytotoxicity; BETULINIC ACID;
D O I：
10.1007/s10600-018-2564-z
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
1-Cyano-2,3-seco-18H-oleanane 3-ethyl-3-ketone was synthesized and underwent base-catalyzed intramolecular oxo-nitrile C(1)-C(3) cyclization to produce the A-pentacyclic 1-cyano-3-ethyl-1(3)-alkene. Nitrile-anionic C(1)-C(31) cyclization of the Br-substituted 3-ethyl-3-ketone occurred with loss of the cyano group and formation of an ,-unsaturated ketone in a six-membered ring A. The cytotoxic properties of the synthesized compounds against cultures of tumor cell lines HEp-2, HCT 116, MS, RD TE32, A549, MCF-7, and PC3 were studied.
引用
收藏
页码：1094 / 1099
页数：6
相关论文
共 50 条
  • [31] DBU-mediated regioselective intramolecular cyclization/dehydration of ortho diketo phenoxyethers: a synthesis of 2,3-substituted γ-benzopyranones
    Bensulong, Sofia
    Boonsombat, Jutatip
    Ruchirawat, Somsak
    TETRAHEDRON, 2013, 69 (44) : 9335 - 9348
  • [32] Synthesis of Indolo[2,3-b]quinolines via a Visible Light-Induced Intramolecular Oxidative Cyclization and Detosylation
    You, F. B.
    Wang, J. G.
    Osman, S.
    Xia, X. D.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (06) : 1048 - 1058
  • [33] Synthesis of Indolo[2,3-b]quinolines via a Visible Light-Induced Intramolecular Oxidative Cyclization and Detosylation
    F. B. You
    J. G. Wang
    S. Osman
    X. D. Xia
    Russian Journal of Organic Chemistry, 2023, 59 : 1048 - 1058
  • [34] Synthesis of 2,3-dihydro-1H-pyrroles by intramolecular cyclization of N-(3-butynyl)sulfonamides
    Chung, Min-Ching
    Chan, Yung-Hsiang
    Chang, Wen-Jung
    Hou, Duen-Ren
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (17) : 3783 - 3790
  • [35] Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization
    Fugard, Alison J.
    Thompson, Bethany K.
    Slawin, Alexandra M. Z.
    Taylor, James E.
    Smith, Andrew D.
    ORGANIC LETTERS, 2015, 17 (23) : 5824 - 5827
  • [36] Synthesis of 2,3-Seco-Derivatives of Dihydrobetulonic Acid and its Methyl Ester
    Krainova, G. F.
    Gagarskikh, O. N.
    Grishko, V. V.
    CHEMISTRY OF NATURAL COMPOUNDS, 2022, 58 (04) : 693 - 698
  • [37] Zeolite-catalyzed synthesis of 2,3-unsubstituted benzo[b]furans via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals
    Sun, Nan
    Huang, Peng
    Wang, Yifan
    Mo, Weimin
    Hu, Baoxiang
    Shen, Zhenlu
    Hu, Xinquan
    TETRAHEDRON, 2015, 71 (29) : 4835 - 4841
  • [38] Cascade Synthesis of Thieno[2,3-b] pyridines by Using Intramolecular Cyclization Reactions of 3-Cyano-2-(organylmethylthio)pyridines
    Alinaghizadeh, Fatemeh
    Zahedifar, Mahboobeh
    Seifi, Mohammad
    Sheibani, Hassan
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2016, 27 (04) : 663 - 669
  • [39] 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
  • [40] Synthesis of 2,3-Seco-Derivatives of Dihydrobetulonic Acid and its Methyl Ester
    G. F. Krainova
    O. N. Gagarskikh
    V. V. Grishko
    Chemistry of Natural Compounds, 2022, 58 : 693 - 698
12345