New Chiral Ebselen Analogues with Antioxidant and Cytotoxic Potential.
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.
['Pacuła|Agata J|AJ|', 'Kaczor|Katarzyna B|KB|', 'Antosiewicz|Jędrzej|J|', 'Janecka|Anna|A|', 'Długosz|Angelika|A|', 'Janecki|Tomasz|T|', 'Wojtczak|Andrzej|A|', 'Ścianowski|Jacek|J|']
D000970:Antineoplastic Agents D000975:Antioxidants D001393:Azoles D002384:Catalysis D045744:Cell Line, Tumor D049109:Cell Proliferation D006801:Humans D054833:Isoindoles D061986:MCF-7 Cells D015394:Molecular Structure D009930:Organic Chemicals D016566:Organoselenium Compounds D013844:Thiazoles
antioxidant activity biological activity organoselenium compounds terpenes