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

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.

SUBMITTER: Das J 

PROVIDER: S-EPMC3876475 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature