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

Authors :: Das J
Bhan A
Mandal SS
Lovely CJ
Source :: Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2013 Nov 15; Vol. 23 (22), pp. 6183-7. Date of Electronic Publication: 2013 Sep 06.
Publication Year :: 2013
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.<br /> (Copyright © 2013 Elsevier Ltd. All rights reserved.)

Subjects :: Alkaloids chemistry
Animals
Biomimetic Materials chemical synthesis
Biomimetic Materials chemistry
Biomimetic Materials pharmacology
Imidazoles chemistry
Molecular Structure
Naphthoquinones chemistry
Oxidation-Reduction
Porifera chemistry
Stereoisomerism
Alkaloids chemical synthesis
Alkaloids pharmacology
Imidazoles chemical synthesis
Imidazoles pharmacology
Naphthoquinones chemical synthesis
Naphthoquinones pharmacology

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