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Planta Med 1997; 63(6): 544-547
DOI: 10.1055/s-2006-957760
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*
* Part 93 in the series “Acetogenic Isoquinoline Alkaloids”. For Part 92, see ref. (1).Weitere Informationen
Publikationsverlauf
1996
1997
Publikationsdatum:
04. Januar 2007 (online)
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