Anticancer and antimicrobial evaluation of newly synthesized steroidal 5,6 fused benzothiazines

Abstract

A series of new 5α-cholestano [5,6-b] benzothiazines (4-6) has been synthesized by the reaction of 5α-cholestan-6-one (1-3) with 2-aminothiophenol in the presence of iodine. The structures of newly synthesized compounds have been established on the basis of spectral and analytical data. Compounds (1-6) were screened for in vitro anticancer activity against the human cancer cell lines; SW480 (colon adenocarcinoma cells), A549 (lung carcinoma cells), HepG2 (hepatic carcinoma cells) and HeLa (cervical cancer cells) using MTT assay during which the products (4-6) showed marked increase in anticancer activity and in particular, compound 6 showed IC50=13.73μmolL-1 against HeLa cells, being more effective than Doxorubicin against the same cells. Compounds 4 and 6 also showed minimum IC50 of 15.83μmolL-1 and 16.89μmolL-1 against HepG2 and A549 cells, respectively. Compounds (1-6) were also tested for in vitro antimicrobial activity against different bacterial as well as fungal strains during which newly synthesized compounds (4-6) were found more potent than starting compounds (1-3). Compound 4 was found to be more potent than the reference drug, Chloramphenicol, in the case of Escherichia coli while compound 5 was found almost equally potential antifungal agent against P. marneffei in comparison with the reference drug, Nystatin. © 2013 .