Materials, Vol. 12, Pages 3579: Bioselectivity Induced by Chirality of New Terpenyl Organoselenium Compounds

Research paper by Magdalena Obieziurska, Agata J. Pacuła, Angelika Długosz-Pokorska, Marek Krzemiński, Anna Janecka, Jacek Ścianowski

Indexed on: 04 Nov '19Published on: 31 Oct '19Published in: Materials


A series of new chiral benzisoselenazol-3(2H)-ones substituted on the nitrogen atom with three monoterpene moieties—p-menthane, pinane and carane—was synthesized. The compounds were obtained by the reaction of 2-(chloroseleno)benzoyl chloride with an appropriate terpene amine, first synthesized by a multistep methodology starting from the corresponding alcohol (p-menthane system) or alkene (pinene and carene systems). Compounds were tested as antioxidants and anticancer agents. The N-isopinocampheyl-1,2-benzisoselenazol-3(2H)-one was the best peroxide scavenger and antiproliferative agent on the human promyelocytic leukemia cell line HL-60. The N-menthyl-1,2-benzisoselenazol-3(2H)-one revealed the highest anticancer potential towards breast cancer line MCF-7. The influence of structure and chirality on the bio-activity of the obtained organoselenium compounds was thoroughly evaluated.