Pacuła Agata J, Kaczor Katarzyna B, Antosiewicz Jędrzej, Janecka Anna, Długosz Angelika, Janecki Tomasz, Wojtczak Andrzej, Ścianowski Jacek
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, Gagarina 7, 87-100 Torun, Poland.
Department of Bioenergetics and Physiology of Exercise, Medical University of Gdansk, Debinki 1, 80-211 Gdansk, Poland.
Molecules. 2017 Mar 20;22(3):492. doi: 10.3390/molecules22030492.
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.
新型手性莰烷衍生的苯并异硒唑-3(2H)-酮及相应的二硒化物已通过简便的一锅法合成。Se-N键能有效地转化为Se-Se键，且该键也能很容易地重新氧化为初始的苯并异硒唑酮部分。对樟脑衍生物的抗氧化活性进行了评估，并与一系列通过改进方法（包括改进二硒代双（二苯甲酸）的合成和分离）获得的N-氨基酸苯并异硒唑-3(2H)-酮的反应活性进行了比较。最有效的过氧化物清除剂，即N-冰片基和N-亮氨酸甲酯苯并异硒唑-3(2H)-酮，进一步作为细胞毒性剂在四种癌细胞系（MCF-7、HEP G2、HL 6和DU 145）和正常细胞系PNT1A上进行了评估。对带有3-甲基丁基碳链的两种化合物，即N-亮氨酸甲酯和N-3-甲基丁基苯并异硒唑-3(2H)-酮，评估了其最高的抗增殖潜力。
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