Abstract

Stereoselective synthesis of (Z)-methyl 2-[(Z)-3-substituted 2-[2-(2,4-dinitrophenyl)hydrazono]-4-oxothiazolidine-5-ylidene]acetates and (Z)-methyl 2-[(Z)-3-substituted 2-[2-(tosylhydrazono)-4-oxothiazolidine-5-ylidene]acetates via the cyclization of N-substituted 2-arylhydrazino-carbothioamides with dialkyl acetylenedicarboxylates in absolute ethanol is reported. The structures were confirmed by spectroscopic data as well as single-crystal X-ray analyses. The mechanism of nucleophilic addition and the role of electronic factors were discussed. The anticancer activity of the newly synthesized compounds was evaluated against a panel of 60 cell lines derived from 9 different types of cancers including, leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers and the results revealed that the cyclohexyl derivative has a significant broad anticancer activity, especially against different leukemia and colon cancer cell lines.

Graphic abstract

中文翻译：

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立体选择性合成2-（2,4-二硝基苯基）hydr-和（2-甲苯磺酰hydr）-4-氧代-噻唑烷衍生物并筛选其抗癌活性

摘要

（Z）-甲基2-[（（Z））-3-取代的2- [2-（2-（2,4-二硝基苯基）hydr] 4-氧噻唑烷-5-亚烷基]乙酸酯和（Z）-甲基2-的立体选择性合成[（Z）-3-取代的2- [2-（甲苯磺酰肼基）-4-氧噻唑烷-5-亚烷基]乙酸酯通过N的环化反应据报道在无水乙醇中用乙炔二羧酸二烷基酯取代了2-芳基肼基-碳硫酰胺。通过光谱数据以及单晶X射线分析证实了结构。亲核加成的机理和电子因素的作用进行了讨论。对新合成化合物的抗癌活性进行了评估，其针对来自9种不同类型癌症（包括白血病，黑色素瘤，肺癌，结肠癌，CNS，卵巢癌，肾癌，前列腺癌和乳腺癌）的60种细胞系进行了评估，结果表明：环己基衍生物具有显着的广泛的抗癌活性，尤其是针对不同的白血病和结肠癌细胞系。

图形摘要