Total syntheses and cytotoxicity of kealiiquinone, 2-deoxy-2-aminokealiiquinone and analogs.
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.
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019, United States.
Jayanta
J
Das
Arunoday
A
Bhan
Subhrangsu S
SS
Mandal
Carl J
CJ
Lovely
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010084:Oxidation-Reduction; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D007093:Imidazoles; D009285:Naphthoquinones
Biomimetic; Cytotoxicity; Leucetta alkaloids; Naphthimidazole; Oxidation