Synthesis and Intramolecular Cyclization of 2,3-Seco-Lupane Triterpenoids with an Ethylketone Fragment

被引：0

作者：

Galaiko, N. V. ^{[1
]}

Beloglazova, Yu. A. ^{[1
]}

Grishko, V. V. ^{[1
]}

机构：

[1] Russian Acad Sci, Inst Tech Chem, Ural Branch, Perm 614013, Russia

来源：

CHEMISTRY OF NATURAL COMPOUNDS | 2023年 / 59卷 / 01期

基金：

俄罗斯科学基金会;

关键词：

A-secotriterpenoids; dihydrobetulonic acid; Beckmann rearrangement; nitrile-anionic cyclization; ethylketone; cytotoxic activity; BETULINIC ACID;

D O I：

10.1007/s10600-023-03925-9

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A 1-cyano-2,3-secolupane derivative with an ethylketone fragment was synthesized from 2-hydroxyoximodihydrobetulonic acid methyl ester via a Grignard reaction followed by a Beckmann rearrangement and was used further to prepare alpha-bromo-substituted diastereomers. Nitrile-anionic cyclization of the ethylketone and alpha-bromo isomers produced cyclic derivatives with an alkenenitrile and an alpha,beta-unsaturated ketone in ring A, respectively. The obtained compounds did not exhibit cytotoxic activity according to biological screening data.

引用

页码：94 / 98

页数：5

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