Total syntheses and cytotoxicity of kealiiquinone, 2-deoxy-2-aminokealiiquinone and analogs

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷:23

Article

Das, Jayanta¹  Bhan, Arunoday¹  Mandal, Subhrangsu S.¹  Lovely, Carl J.¹ 

[1] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA

关键词: Naphthimidazole;    Biomimetic;    Oxidation;    Cytotoxicity;    Leucetta alkaloids;   

DOI  :  10.1016/j.bmcl.2013.08.093

来源: Elsevier

【 摘 要 】

Concise syntheses of two Leucetta-derived naphthimidazole alkaloids, kealiiquinone and 2-deoxy-2-aminokealiiquinone, are described based on a biosynthetic-guided hypothesis. Advanced intermediates containing the full naphthimidazole framework are constructed through Friedel-Crafts chemistry followed by oxidation of the electron rich C-ring with hydrogen peroxide. The cytotoxicity of these alkaloids in a breast cancer cell line along with several closely related marine-derived natural products kealiinines A-C and analogs are reported. (c) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

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