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Molecules 2017, 22(3), 492; doi:10.3390/molecules22030492

New Chiral Ebselen Analogues with Antioxidant and Cytotoxic Potential

1
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, Gagarina 7, 87-100 Torun, Poland
2
Department of Bioenergetics and Physiology of Exercise, Medical University of Gdansk, Debinki 1, 80-211 Gdansk, Poland
3
Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland
4
Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland
5
Department of Biochemistry, Gdansk University of Physical Education and Sport, Kazimierza Gorskiego 1, 80-336 Gdansk, Poland
*
Author to whom correspondence should be addressed.
Received: 30 January 2017 / Revised: 14 March 2017 / Accepted: 17 March 2017 / Published: 20 March 2017
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Abstract

New chiral camphane-derived benzisoselenazol-3(2H)-ones and corresponding diselenides have been synthetized using a convenient one-pot procedure. Se-N bond was efficiently converted to an Se-Se bond, which could also be easily re-oxidized to the initial benzisoselenazolone moiety. The antioxidant activity of camphor derivatives was evaluated and compared to the reactivity of a series of N-amino acid benzisoselenazol-3(2H)-ones obtained by a modified procedure involving the improved synthesis and isolation of the diseleno bis(dibenzoic) acid. The most efficient peroxide scavengers, N-bornyl and N-leucine methyl ester benzisoselenazol-3(2H)-ones, were further evaluated as cytotoxic agents on four cancer cell lines (MCF-7, HEP G2, HL 6, and DU 145) and normal cell line PNT1A. The highest antiproliferative potential was evaluated for two compounds bearing a 3-methylbutyl carbon chain, N-leucine methyl ester and N-3-methylbutyl benzisoselenazol-3(2H)-ones. View Full-Text
Keywords: organoselenium compounds; terpenes; antioxidant activity; biological activity organoselenium compounds; terpenes; antioxidant activity; biological activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Pacuła, A.J.; Kaczor, K.B.; Antosiewicz, J.; Janecka, A.; Długosz, A.; Janecki, T.; Wojtczak, A.; Ścianowski, J. New Chiral Ebselen Analogues with Antioxidant and Cytotoxic Potential. Molecules 2017, 22, 492.

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