title: N,N-dimethyldioncophyllinium A iodide: synthesis, stereoanalysis, and antimalarial activity of the first N-quaternary naphthylisoquinolinium salt.
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.
authors.affiliation: Institut für Organische Chemie, Universität, Am Hubland, Würzburg, Germany.
authors.forename: G
authors.initials: G
authors.lastname: Bringmann
authors.forename: M
authors.initials: M
authors.lastname: Ochse
authors.forename: M
authors.initials: M
authors.lastname: Schäffer
authors.forename: R
authors.initials: R
authors.lastname: God
authors.forename: R
authors.initials: R
authors.lastname: Walter
authors.forename: G
authors.initials: G
authors.lastname: François
mesh_terms: 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
chemical_list: D000962:Antimalarials; D007546:Isoquinolines; C110582:N,N-dimethyldioncophyllinium A; D009281:Naphthalenes