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. 2017 Mar 20;22(3):492.
doi: 10.3390/molecules22030492.

New Chiral Ebselen Analogues with Antioxidant and Cytotoxic Potential

Agata J Pacuła  1 , Katarzyna B Kaczor  2 , Jędrzej Antosiewicz  3   4 , Anna Janecka  5 , Angelika Długosz  6 , Tomasz Janecki  7 , Andrzej Wojtczak  8 , Jacek Ścianowski  9
Affiliations

New Chiral Ebselen Analogues with Antioxidant and Cytotoxic Potential

Agata J Pacuła et al. Molecules. .

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.

Keywords: antioxidant activity; biological activity; organoselenium compounds; terpenes.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Probable catalytic pathways for the reduction of H2O2 by ebselen.
Scheme 2
Scheme 2
Methodologies to synthesize ebselen 1.
Scheme 3
Scheme 3
Synthesis of N-isobornyl and N-bornyl-o-iodobenzamides 15 and 16.
Scheme 4
Scheme 4
Synthesis of diselenides 17 and 18.
Scheme 5
Scheme 5
Synthesis of N-isobornyl and N-bornyl benzisoselenazol-3(2H)-ones 19 and 20.
Scheme 6
Scheme 6
Cleavage and regeneration of Se-N bond.
Scheme 7
Scheme 7
Synthesis of amino acid derivatives 21–25.
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