6-氨基-2-苯基苯并噻唑新型衍生物的合成与抗肿瘤评价

Synthesis and antitumor evaluation of novel derivatives of 6-amino-2-phenylbenzothiazoles.

作者信息

Racane Livio, Stojkovic Ranko, Tralic-Kulenovic Vesna, Karminski-Zamola Grace

机构信息

Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 30, 10000 Zagreb, Croatia.

出版信息

Molecules. 2006 May 9;11(5):325-33. doi: 10.3390/11050325.

DOI:10.3390/11050325

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6148487/

Abstract

Novel derivatives of 6-amino-2-phenylbenzothiazole bearing different substituents (amino, dimethylamino or fluoro) on the phenyl ring were prepared as the corresponding hydrochloride salts. 6-Nitro-2-(substituted-phenyl)benzothiazoles (1-6) were synthesized by condensation reactions of substituted benzaldehydes with 2-amino-5-nitrothiophenol. Nitro derivatives were reduced to the amino derivatives with SnCl(2)/HCl. Water soluble hydrochloride salts of 6-amino-2-(substituted-phenyl)benzothiazole (13-19)were prepared using concentrated or gaseous HCl. Compounds 13-19 were found to exert cytostatic activities against malignant human cell lines: cervical (HeLa), breast (MCF-7),colon (CaCo-2), laryngeal carcinoma (Hep-2), and normal human fibroblast cell lines (WI-38).

摘要

制备了在苯环上带有不同取代基（氨基、二甲基氨基或氟）的6-氨基-2-苯基苯并噻唑的新型衍生物，它们为相应的盐酸盐。通过取代苯甲醛与2-氨基-5-硝基硫酚的缩合反应合成了6-硝基-2-（取代苯基）苯并噻唑（1-6）。用SnCl₂/HCl将硝基衍生物还原为氨基衍生物。使用浓盐酸或气态氯化氢制备了6-氨基-2-（取代苯基）苯并噻唑（13-19）的水溶性盐酸盐。发现化合物13-19对恶性人类细胞系：宫颈癌细胞（HeLa）、乳腺癌细胞（MCF-7）、结肠癌细胞（CaCo-2）、喉癌细胞（Hep-2）以及正常人类成纤维细胞系（WI-38）具有细胞抑制活性。

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