N,N-dimethyldioncophyllinium A iodide: synthesis, stereoanalysis, and antimalarial activity of the first N-quaternary naphthylisoquinolinium salt.
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.
Bringmann
G
G
Institut für Organische Chemie, Universität, Am Hubland, Würzburg, Germany.
Ochse
M
M
Schäffer
M
M
God
R
R
Walter
R
R
François
G
G
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects; D013237:Stereoisomerism
D000962:Antimalarials; D007546:Isoquinolines; C110582:N,N-dimethyldioncophyllinium A; D009281:Naphthalenes