新型 5-甲硫基偶氮并[1,5-a]嘧啶-7(4H)-酮的合成及其化学和细胞毒性研究

IF 1.4 4区化学 Q3 CHEMISTRY, ORGANIC

Chemistry of Heterocyclic Compounds Pub Date : 2024-04-06 DOI:10.1007/s10593-024-03293-4

Daniil N. Lyapustin, Dilya F. Fayzullina, Irina V. Marusich, Svetlana K. Kotovskaya, Vsevolod V. Melekhin, Maria D. Tokhtueva, Evgeny N. Ulomsky, Vladimir L. Rusinov

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引用次数: 0

摘要

通过 3-氨基唑和 5-[双(甲硫基)亚甲基]-2,2-二甲基-1,3-二氧六环-4,6-二酮的杂环化反应，开发了一种合成新型 5-甲硫基偶氮并[1,5-a]嘧啶-7(4H)-酮的方法。在优化过程中分离出了 5-甲硫基-7-氧代-4,7-二氢唑并[1,5-a]嘧啶-6-羧酸，这使我们能够确定该杂环化反应的转化顺序。我们研究了所生成的 5-甲硫基氮杂并[1,5-a]嘧啶-7(4H)-酮在经典亲电取代反应中的反应性。评估了这些化合物对 A549、HepG2 和 RD 肿瘤细胞系以及正常 HEK-293 细胞的细胞毒性作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

A synthesis of novel 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones and investigation of their chemical and cytotoxic properties

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A synthesis of novel 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones and investigation of their chemical and cytotoxic properties

A method for the synthesis of novel 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones by heterocyclization of 3-aminoazoles and 5-[bis(methylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones was developed. 5-Methylsulfanyl-7-oxo-4,7-dihydroazolo- [1,5-a]pyrimidine-6-carboxylic acid was isolated during optimization of the process, which allowed us to establish the sequence of transformations of this heterocyclization reaction. The reactivity of the resulting 5-methylsulfanylazolo[1,5-a]pyrimidin-7(4H)-ones in classical electrophilic substitution reactions was studied. The cytotoxic effect of these compounds toward A549, HepG2, and RD tumor cell lines as well as normal HEK-293 cells was assessed.

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来源期刊

Chemistry of Heterocyclic Compounds 化学-有机化学

CiteScore

2.90

自引率

13.30%

发文量

审稿时长

1 months

期刊介绍： The international journal Chemistry of Heterocyclic Compounds publishes original papers, short communications, reviews, and mini-reviews dealing with problems in the field of heterocyclic chemistry in Russian and English. The Journal also publishes reviews and annotations on new books and brief reports on conferences in the field of heterocyclic chemistry, as well as commemoratives dedicated to prominent heterocyclic chemists.