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Anti-proliferative and morphological studies of 2-(benzo[d]thiazol-2-yl) derivatives together with their strategy in ionic liquids immobilized reactions
Journal of the Iranian Chemical Society ( IF 2.2 ) Pub Date : 2024-03-19 , DOI: 10.1007/s13738-023-02956-x
Rafat M. Mohareb , Rehab A. Ibrahim , Fatma O. Al Farouk

In this work, an efficient and expeditious synthesis of a series of new benzo[d]thiazole derivatives has been reported starting from the reaction of 2-aminothiophenol with different esters such as ethyl cyanoacetate, diethylmalonate or ethyl acetoacetate to produce benzo[d]thiazole derivatives. The latter compounds underwent multi-component reactions with aromatic aldehydes and cyclohexan-1,3-dione using two different conditions first the use of solvent and regular catalyst and secondly using solvent free ionic liquids immobilized multi-component was studied. Comparison between the yields in the two methods was recorded. The benzo[d]thiazole derivatives were characterized by extensive analytical and spectral studies and were further used as starting materials for some heterocyclic transformations to produce biologically active compounds. Most of the tested compounds exhibited high cytotoxicity except few compounds. All tested compounds exhibited greater inhibitory action than the reference drug Doxorubicin against HeLa cell line except six compounds. The most cytotoxic compounds were 8h, 10e, 12b, 12i, 14b, 14h, 14i and 15i with IC50’s 0.21, 0.26, 0.32, 0.19, 0.32, 0.27, 0.25 and 0.18 µM, respectively against HepG2 cell line. In addition, the majority of the tested compounds emerged as c-MET kinase and PC-3 cell inhibitors which revealed that most of the tested compounds showed from moderate to good inhibitions.



中文翻译:

2-(苯并[d]噻唑-2-基)衍生物的抗增殖和形态学研究及其在离子液体固定化反应中的策略

在这项工作中,报道了从2-氨基苯硫酚与不同的酯(例如氰基乙酸乙酯、丙二酸二乙酯或乙酰乙酸乙酯)反应生成苯并[ d ]噻唑开始,高效、快速地合成了一系列新型苯并[ d ]噻唑衍生物。衍生物。后者化合物在两种不同的条件下与芳香醛和1,3-环己酮进行多组分反应,首先使用溶剂和常规催化剂,其次使用无溶剂离子液体固定多组分。记录两种方法的产量之间的比较。苯并[ d ]噻唑衍生物通过广泛的分析和光谱研究进行了表征,并进一步用作一些杂环转化的起始材料以生产生物活性化合物。除少数化合物外,大多数受试化合物均表现出较高的细胞毒性除六种化合物外,所有测试化合物对 HeLa 细胞系均表现出比参比药物阿霉素更强的抑制作用。最具细胞毒性的化合物是8h10e12b12i14b14h14i15i ,针对 HepG2 细胞系的IC 50分别为 0.21、0.26、0.32、0.19、0.32、0.27、0.25 和 0.18 µM。此外,大多数测试化合物都是 c-MET 激酶和 PC-3 细胞抑制剂,这表明大多数测试化合物表现出中等至良好的抑制作用。

更新日期:2024-03-19
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