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One-pot synthesis of new benzo[4,5]imidazo[2,1-b]pyrimido[4,5-d][1,3] thiazine-2,4(3H)-dione and benzo[4,5]imidazo[2,1-b][1,3]thiazin-4-one derivatives as new anti-cancer components
Journal of Molecular Structure ( IF 4.0 ) Pub Date : 2022-08-29 , DOI: 10.1016/j.molstruc.2022.134037
Nasim Batooie , Mohammad Mehdi Khodaei , Kiumars Bahrami , Seyyed Shahram Miraghaee , Nouraddin Hosseinzadeh , Soraya Sajadimajd

An efficient and one-pot process has been developed for the synthesis of novel benzo[4,5]imidazo[2,1-b]pyrimido[4,5-d][1,3]thiazine-2,4(3H)-diones and benzo[4,5]imidazo[2,1-b][1,3]thiazin-4-ones from CH acids, aldehydes and 2-mercaptobenzimidazole using hexyltriphenylphosphonium bromide ionic liquid (HTPB) as a green promoter and solvent at ambient temperature. The reaction afforded products in high yields and short reaction times, bypassing the conventional harsh reaction conditions and without the need for using volatile solvents. In addition, we evaluated the anti-cancer activity of these compounds on different cancer cells, including A431, PC3, and Panc1 and HDF (human dermal fibroblast) normal cells. Notably, we found that these synthesized compounds have prominent anti-cancer effects on skin, prostate, and pancreatic cancers.



中文翻译:

一锅法合成新的苯并[4,5]咪唑并[2,1-b]嘧啶并[4,5-d][1,3]噻嗪-2,4(3H)-二酮和苯并[4,5]咪唑并[2,1-b][1,3]噻嗪-4-酮衍生物作为新型抗癌成分

开发了一种高效的一锅法合成新型苯并[4,5]咪唑并[2,1 - b ]嘧啶并[4,5 - d ][1,3]噻嗪-2,4(3H) -二酮和苯并[4,5]咪唑[2,1- b][1,3]thiazin-4-ones 来自 CH 酸、醛和 2-巯基苯并咪唑,在环境温度下使用溴化己基三苯基鏻离子液体 (HTPB) 作为绿色促进剂和溶剂。该反应以高收率和短反应时间提供产物,绕过了传统的苛刻反应条件,并且不需要使用挥发性溶剂。此外,我们评估了这些化合物对不同癌细胞的抗癌活性,包括 A431、PC3、Panc1 和 HDF(人真皮成纤维细胞)正常细胞。值得注意的是,我们发现这些合成的化合物对皮肤癌、前列腺癌和胰腺癌具有显着的抗癌作用。

更新日期:2022-08-29
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