22-降-豆甾-22-含氮化合物的合成及抗肿瘤活性

doi:10.11944/j.issn.1000-0518.2015.03.140202

摘要/Abstract

摘要：

从豆甾醇出发,通过3-位羟基及5-位双键保护, 22-位双键臭氧化,得到3-乙酰氧基胆甾-5-烯-22-醛(4)。化合物4进一步与氨基脲、氨基硫脲缩合得到22-降豆甾-22-含氮衍生物,合成物结构经NMR、IR及MS等技术手段进行了表征。并采用6种不同的肿瘤细胞,利用MTT法对合成物进行体外抗肿瘤活性研究,结果表明,具有22-缩氨硫脲基的化合物8具有很好的体外抗肿瘤活性,其对MGC 7901、Hela、SMMC 7404及CNE-2细胞的IC₅₀值分别为10.5、11.6、8.7及11.9。

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关键词: 22-降-豆甾-22-含氮化合物, 抗肿瘤活性, 合成.

Abstract:

Using stigmasterol as a starting material, 3β-acetoxycholest-5-ene-22-al was obtained by the protection of 3-hydroxyl and 5-double bond prior to the ozonolysis of 22-ene. Some 22-abeo-stigmast-22-nitrogen-containing compounds were synthesized by the condensation of aldehydes with semicarbazides and thiosemicarbazides. The structure of compounds were confirmed with NMR, IR and MS. Their antiproliferative activities against six kinds of cancer cells were evaluated with MTT method. Compound 8 with the 22-thiosemicarbazone group exhibits significant inhibitory activity on MGC 7901, Hela, SMMC 7404 and CNE-2 cells with the IC₅₀ values of 10.5, 11.6, 8.7 and 11.9 μmol/L, respectively.

Key words: 22-abeo-stigmast-22-nitrogen-containing compounds, antiproliferative activity, synthesis

中图分类号:

杨雷, 范良华, 赵丹丹, 戚斌斌, 甘春芳, 崔建国, 黄燕敏. 22-降-豆甾-22-含氮化合物的合成及抗肿瘤活性[J]. 应用化学, 2015, 32(3): 273-277.

YANG Lei, FAN Lianghua, ZHAO Dandan, QI Binbin, GAN Chunfang, CUI Jian'guo, HUANG Yanmin. Synthesis and Antiproliferative Activity of 22-Abeo-stigmast-22-nitrogen-containing Compounds[J]. Chinese Journal of Applied Chemistry, 2015, 32(3): 273-277.

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