Water-dependent synthesis of biologically active diaryl diselenides

Abstract

A new one-step method for the synthesis of diaryl diselenides has been developed. The reaction of o-iodobenzamides with dilithium diselenide can be controlled by the presence of water providing a simple and efficient protocol to obtain benzisoselenazolones or diaryl diselenides. A series of N-Aryl ebselen derivatives and the corresponding diselenides was obtained. All synthesized compounds were tested in vitro as antioxidants and cytotoxic agents. N-(2,3,4-Trimethoxyphenyl)benzisoselenazol-3(2H)-one was the best in vitro antioxidant and the corresponding diselenide the most potent cytotoxic agent against prostate cancer cell line DU145, being inactive towards healthy prostate cell line PNT1A. Formula parented.