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
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