SYNTHESIS OF 4-(4-METHYLIDENE-4H-3,1-BENZOTHIAZIN-2-YL)-BENZENE-1,3-DIOLS AND THEIR ANTIPROLIFERATIVE ACTIVITY AGAINST HUMAN CANCER CELL LINES

© 2016 J. Matysiak*^{, #}, A. Skrzypek*, A. Niewiadomy*^, **, M. M. Karpi ska**, J. Wietrzyk***, B. Paw****, D. K opotowska***

^#E-mail: [email protected]

*Department of Chemistry, University of Life Sciences in Lublin, Akademicka 15, 20-950 Lublin, Poland;
**Institute of Industrial Organic Chemistry, Annopol 6, 03-236 Warsaw, Poland;
***Department of Experimental Oncology, Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, R. Weigla 12, 53-114 Wroclaw, Poland;
****Medical University of Lublin, Department of Medicinal Chemistry, Jaczewskiego 4, 20-090 Lublin, Poland

Received March 30, 2015; in final form, September 4, 2015

One-step synthesis of novel biologically active 4- or 6-(4-methylidene-4H-3,1-benzothiazin-2-yl)benzene-1,3-diols is described. The target compounds were prepared by the reaction of aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione]s with 1-(2-aminophenyl)ethanones. Newly synthesized compounds were characterized by IR, ¹H NMR, and mass spectral data. Their antiproliferative potency against human cancer cell lines was determined. Some descriptors were calculated to find the relationship between the structure and activity. It is revealed that the presence of hydrophobic substituents in the benzenediol ring intensifies the biological potency.

Keywords: 4H-3,1-benzothiazine, antiproliferative activity.

Биоорг. химия 2016, 42 (1): 104-110