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N-Terpenyl benzisoselenazolones - evaluation of the particular structure-bioactivity relationship
1 , 1 , 1 , 2 , 1 , 2 , * 1
1  Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
2  Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland


Different activity of compounds with the same molecular formula but possessing alternative bonding arrangement or orientation of atoms in space is a very important issue when constructing molecules that can selectively interact with certain domains of the biological target. Herein, we present the synthesis of new chiral benzisoselenazol-3(2H)-ones substituted on the nitrogen atom with three monoterpene moieties: p-menthane, pinane and carane. All derivatives were obtained by the reaction of appropriate amine with 2-(chloroseleno)benzoyl chloride. The applied terpenyl amines were first synthetized by a multistep procedure starting from corresponding alcohol (p-menthane system) or alkene (pinene and carene systems). Finally, all compounds were tested as antioxidants and antiproliferative agents on breast cancer MCF-7 and human promyelocytic leukemia cell line HL-60. The correlation between the structure of the obtained organoselenium compounds, representing examples of various isomers including enantiomers, diastereoisomers and regioisomers, and their bio-activity was thoroughly evaluated.

Keywords: benzisoselenazol-3(2H)-ones, terpenes, antioxidant activity, antiproliferative activity