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.
Highlights
Organoselenium compounds are well-known for their remarkable redox properties and the ability to act as antioxidants, preventing oxidative stress, as well as pro-oxidants, able to inhibit proliferation of cancer cells [1,2]
The first step of the research involved the synthesis of chiral amines from three monoterpene systems: p-menthane, pinane, and carane
In this paper we have presented the synthesis of the series of N-terpenyl benzisoselenazol-3(2H)4
Summary
Organoselenium compounds are well-known for their remarkable redox properties and the ability to act as antioxidants, preventing oxidative stress, as well as pro-oxidants, able to inhibit proliferation of cancer cells [1,2]. The reactivity can be modulated by transforming the compound to its regioisomer, possessing different atom organization but the same molecular formula. This way the strength of the binding can be changed or affinity for other domains can be developed (Scheme 1). The known optically active benzisoselenazolones on thebenzisoselenazolones bio-capacity of the molecules has not yetalcohol been thoroughly evaluated. The presented research is based on the incorporation of a terpene moiety in the structure of antioxidant and anticancer organoselenium molecules. The benzisoselenazolone core, present in ebselen (N-phenylbenzisoselenazol3(2H)-one), the most studied organoselenium compound with broad spectrum of possible therapeutic. Column chromatography was performed using Merck 40-63D 60Å silica gel (Merck, Darmstadt, Germany) and aluminium oxide
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