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Open AccessArticle

Bioselectivity Induced by Chirality of New Terpenyl Organoselenium Compounds

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
*
Author to whom correspondence should be addressed.
Dedicated to Professor Marek Zaidlewicz on the occasion of his 80th birthday.
Materials 2019, 12(21), 3579; https://doi.org/10.3390/ma12213579
Received: 9 October 2019 / Revised: 24 October 2019 / Accepted: 29 October 2019 / Published: 31 October 2019
(This article belongs to the Special Issue Current Problems of the Organic Chemistry of Sulfur and Selenium)
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. View Full-Text
Keywords: benzisoselenazol-3(2H)-ones; terpenes; antioxidant activity; antiproliferative activity benzisoselenazol-3(2H)-ones; terpenes; antioxidant activity; antiproliferative activity
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MDPI and ACS Style

Obieziurska, M.; Pacuła, A.J.; Długosz-Pokorska, A.; Krzemiński, M.; Janecka, A.; Ścianowski, J. Bioselectivity Induced by Chirality of New Terpenyl Organoselenium Compounds. Materials 2019, 12, 3579.

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