Asymmetric synthesis and anti-protozoal activity of the 8,4'-oxyneolignans virolin, surinamensin and analogues

Eur J Med Chem. 2013 Feb:60:240-8. doi: 10.1016/j.ejmech.2012.12.013. Epub 2012 Dec 16.

Abstract

The asymmetric synthesis of 8,4'-oxyneolignans (-)-virolin, (-)-surinamensin and a number of analogues has been achieved. A divergent synthesis was used, with all compounds being elaborated from a single chiral aldehyde derived from ethyl lactate. In the 15 compounds that were tested, the level of substitution on the A-ring was found to directly influence the activity against Leishmania donovani whilst the activity against Plasmodium falciparum was influenced by numerous substitution and stereochemical factors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anisoles / chemical synthesis
  • Anisoles / chemistry
  • Anisoles / pharmacology*
  • Antiprotozoal Agents / chemical synthesis
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / pharmacology*
  • Leishmania donovani / drug effects*
  • Lignans / chemical synthesis
  • Lignans / chemistry
  • Lignans / pharmacology*
  • Molecular Conformation
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects*

Substances

  • Anisoles
  • Antiprotozoal Agents
  • Lignans
  • virolin
  • surinamensin