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Antineoplastic agents 491. Synthetic conversion of aaptamine to isoaaptamine, 9-demethylaaptamine, and 4-methylaaptamine

  1. Author:
    Pettit, G. R.
    Hoffmann, H.
    Herald, D. L.
    McNulty, J.
    Murphy, A.
    Higgs, K. C.
    Hamel, E.
    Lewin, N. E.
    Pearce, L. V.
    Blumberg, P. M.
    Pettit, R. K.
    Knight, J. C.

  2. Author Address

    Pettit, GR, Arizona State Univ, Canc Res Inst, POB 872404, Tempe, AZ 85287 USA Arizona State Univ, Canc Res Inst, Tempe, AZ 85287 USA. Arizona State Univ, Dept Chem & Biochem, Tempe, AZ 85287 USA. NCI, Screening Technol Branch, DTP, DCTD,NIH, Ft Detrick, MD 21702 USA. NCI, Mol Mechanism Tumor Promot Sect, LCCTP, Bethesda, MD 20892 USA.
    1. Year: 2004
  2. Journal: Journal of Organic Chemistry
    1. 69
    2. 7
    3. Pages: 2251-2256
  4. Type of Article: Article
  1. Abstract:

    Aaptamine (1) was used as starting material for synthetic transformation to isoaaptamine (2), 9-demethylaaptamine (5), and 4-methylaaptamine (6). A general method for the selective O-demethylation of such 1H-benzo [de][1,6]-naphthyridine (1) marine sponge constituents at position C-9 has been developed. Selective O-demethylation of aaptamine (1) and 1-methylaaptamine (11) with 48% hydrobromic acid led to 9-demethylaaptamine (5) and isoaaptamine (2), respectively. A selection of other aaptamine derivatives were synthesized, and their structures were unambiguously determined by X-ray methods. In addition, their cancer cell growth inhibitory properties were evaluated against the murine P388 lymphocytic cell line and a minipanel of human cancer cell lines. Evaluation as inhibitors of the PKC signal transduction pathway and against a selection of microorganisms was also undertaken. Aaptamine derivatives 3 and 5 had broad-spectrum antimicrobial activities

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