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

被引：0
作者：
A. V. Konysheva
A. E. Zhukova
M. V. Dmitriev
V. V. Grishko
机构：
[1] Russian Academy of Sciences,Institute of Technical Chemistry, Ural Branch
[2] Perm State National Research University,undefined
来源：
Chemistry of Natural Compounds | 2018年 / 54卷
关键词：
triterpenoids; allobetulone; Grignard reaction; nitrile-anionic cyclization; oxo-nitrile cyclization; cytotoxicity;
D O I：
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中图分类号：
学科分类号：
摘要：
1-Cyano-2,3-seco-18αH-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 α,β-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.
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页码：1094 / 1099
页数：5
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