| Summary: | A series of new chiral benzisoselenazol-3(2<i>H</i>)-ones and their corresponding diselenides bearing an <i>o</i>-amido function substituted on the nitrogen atom with various aliphatic and aromatic moieties were synthesized. All derivatives representing pairs of enantiomers or diastereoisomers were obtained to thoroughly evaluate the three-dimensional structure–activity correlation. First, bensisoselenazol-3(2<i>H</i>)-ones were synthesized by reacting 2-(chloroseleno)benzoyl chloride with an appropriate enantiomerically pure amine. Then, the Se–N bond was cleaved by a reduction–oxidation procedure using sodium borohydride and then air oxidation to obtain the corresponding diselenides. All derivatives were tested as antioxidants and anticancer agents. In general, the diselenides were more reactive peroxide scavengers, with the highest activity observed for 2,2′-diselenobis[<i>N</i>-(1<i>S</i>,2<i>S</i>)-(-)-<i>trans</i>-2-hydroksy-1-indanylbezamide]. The most cytotoxic derivative towards human promyelocytic leukemia HL-60 and breast cancer MCF-7 cell lines was <i>N</i>-[(1<i>S</i>,2<i>R</i>)-(-)-<i>cis</i>-2-hydroksy-1-indanyl]-1,2-benzizoselenazol-3(2<i>H</i>)-one. The structure–activity relationship of the obtained organoselenium derivatives was discussed.
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