Total syntheses and cytotoxicity of kealiiquinone, 2-deoxy-2-aminokealiiquinone and analogs |
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| Authors: | Jayanta Das Arunoday Bhan Subhrangsu S Mandal Carl J Lovely |
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| Institution: | Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019, United States |
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| Abstract: | 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. |
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| Keywords: | Naphthimidazole Biomimetic Oxidation Cytotoxicity |
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