Competitive N- and O-alkylation of 5-bromo-2-methylthio-6-trifluoromethyluracil as a promising anticancer agent

IF 1.6 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2026-10-17 DOI:10.1007/s11172-026-5102-3

O. E. Melnikov, N. A. Elkina, Ya. V. Burgart, E. V. Shchegolkov, M. A. Ezhikova, M. I. Kodess, A. A. Shitova, O. V. Soldatova, A. S. Filimonov, M. V. Filimonova, V. I. Saloutin

引用次数: 0

Abstract

The synthesis of 5-bromo-2-methylthio-6-(thrifluoromethyl)uracil and its non-fluorinated analog was reported. The preliminary evaluation of their in vivo anticancer activity using a murine solid Ehrlich carcinoma model revealed a significant activity of the trifluoromethyl-containing derivative. The pathways for the modification of the synthesized thiouracils were investigated in the competitive N³- and O-alkylation with haloalkanes with different carbon chain length, the latter being responsible for the ratio of the resulting regioisomers. The conditions favorable for the preferential formation of the N³-isomer were proposed.

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5-溴-2-甲基硫-6-三氟甲基尿嘧啶的竞争性N-和o-烷基化

报道了5-溴-2-甲基硫-6-（三氟甲基）尿嘧啶及其无氟类似物的合成。使用小鼠固体埃利希癌模型对其体内抗癌活性进行初步评估，结果显示含有三氟甲基的衍生物具有显著的活性。研究了合成的硫脲嘧啶与不同碳链长度的卤代烷竞争性的N3-烷基化和o -烷基化的修饰途径，后者决定了生成的区域异构体的比例。提出了有利于n3 -异构体优先形成的条件。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.