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.
Original language | English (US) |
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Pages (from-to) | 2251-2256 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 69 |
Issue number | 7 |
DOIs | |
State | Published - Apr 2 2004 |
ASJC Scopus subject areas
- Organic Chemistry
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CCDC 240771: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Hoffmann, H. (Creator), Herald, D. L. (Creator), McNulty, J. (Creator), Murphy, A. (Creator), Higgs, K. C. (Creator), Hamel, E. (Creator), Lewin, N. E. (Creator), Pearce, L. V. (Creator), Blumberg, P. M. (Creator), Pettit, R. K. (Creator) & Knight, J. C. (Creator), The Cambridge Structural Database, 2004
DOI: 10.5517/cc82jtn, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc82jtn&sid=DataCite
Dataset
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CCDC 240773: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Hoffmann, H. (Creator), Herald, D. L. (Creator), McNulty, J. (Creator), Murphy, A. (Creator), Higgs, K. C. (Creator), Hamel, E. (Creator), Lewin, N. E. (Creator), Pearce, L. V. (Creator), Blumberg, P. M. (Creator), Pettit, R. K. (Creator) & Knight, J. C. (Creator), The Cambridge Structural Database, 2004
DOI: 10.5517/cc82jwq, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc82jwq&sid=DataCite
Dataset
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CCDC 240772: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Hoffmann, H. (Creator), Herald, D. L. (Creator), McNulty, J. (Creator), Murphy, A. (Creator), Higgs, K. C. (Creator), Hamel, E. (Creator), Lewin, N. E. (Creator), Pearce, L. V. (Creator), Blumberg, P. M. (Creator), Pettit, R. K. (Creator) & Knight, J. C. (Creator), The Cambridge Structural Database, 2004
DOI: 10.5517/cc82jvp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc82jvp&sid=DataCite
Dataset