N,N-Dimethyldioncophyllinium A Iodide: Synthesis, Stereoanalysis, and Antimalarial Activity of the First N-Quaternary Naphthylisoquinolinium Salt*

Gerhard Bringmann; Michael Ochse; Manuela Schäffer; Ralf God; Rainer Walter; Guido François

doi:10.1055/s-2006-957760

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Planta Med 1997; 63(6): 544-547
DOI: 10.1055/s-2006-957760

Papers

Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

N,N-Dimethyldioncophyllinium A Iodide: Synthesis, Stereoanalysis, and Antimalarial Activity of the First N-Quaternary Naphthylisoquinolinium Salt*

Gerhard Bringmann¹ , Michael Ochse¹ , Manuela Schäffer¹ , Ralf God¹ , Rainer Walter¹ , Guido François²

¹Institut für OrganischeChemie der Universität, Am Hubland, D-97074 Würzburg, Germany
²Prins Leopold Instituut voor Tropische Geneeskunde, Nationalestraat 155, B-2000 Antwerpen, Belgium

* Part 93 in the series “Acetogenic Isoquinoline Alkaloids”. For Part 92, see ref. (1).

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Publication History

1996

1997

Publication Date:
04 January 2007 (online)

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Abstract

The first synthesis of an N-quaternary salt of a naphthylisoquinoline alkaloid, N,N-dimethyldioncophyllinium A iodide, is described. For this potential natural product, a degradative procedure for the unambiguous stereoanalysis of the stereogenic centers has been elaborated. It shows enhanced anti-plasmodial activity in vitro towards Plasmodium falciparum erythrocytic forms, as compared to its less methylated precursors.

Key words

Ancistrocladaceae - Dioncophyllaceae - naphthylisoquinoline alkaloids - N-quaternary isoquinolinium salts - oxidative degradation - stereoanalysis - antimalarial activity - Plasmodium falciparum

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