N,N-dimethyldioncophyllinium A iodide: synthesis, stereoanalysis, and antimalarial activity of the first N-quaternary naphthylisoquinolinium salt

Planta Med. 1997 Dec;63(6):544-7. doi: 10.1055/s-2006-957760.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / chemistry
  • Antimalarials / pharmacology
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry
  • Isoquinolines / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry
  • Naphthalenes / pharmacology
  • Plasmodium falciparum / drug effects
  • Stereoisomerism

Substances

  • Antimalarials
  • Isoquinolines
  • N,N-dimethyldioncophyllinium A
  • Naphthalenes