Synthesis and Antitumor Evaluation of Novel Derivatives of 6-Amino-2-phenylbenzothiazoles

Abstract

Novel derivatives of 6-amino-2-phenylbenzothiazole bearing differentsubstituents (amino, dimethylamino or fluoro) on the phenyl ring were prepared as thecorresponding hydrochloride salts. 6-Nitro-2-(substituted-phenyl)benzothiazoles (1-6) weresynthesized by condensation reactions of substituted benzaldehydes with 2-amino-5-nitrothiophenol. Nitro derivatives were reduced to the amino derivatives with SnCl2/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 exertcytostatic 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).

Keywords

• Benzothiazole synthesis
• antitumor activity.