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Bioselectivity Induced by Chirality of New Terpenyl Organoselenium Compounds.

ABSTRACT: 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.

SUBMITTER: Obieziurska M

PROVIDER: S-EPMC6862013 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Bioselectivity Induced by Chirality of New Terpenyl Organoselenium Compounds.

Obieziurska Magdalena M Pacuła Agata J AJ Długosz-Pokorska Angelika A Krzemiński Marek M Janecka Anna A Ścianowski Jacek J

Materials (Basel, Switzerland) 20191031 21

A series of new chiral benzisoselenazol-3(2H)-ones substituted on the nitrogen atom with three monoterpene moieties-<i>p</i>-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 (<i>p</i>-menthane system) or alkene (pinene and carene systems). Compounds were tested as antioxidants and anticancer agents. The ...[more]

PMID: 31683558

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