Novel spiroanellated 1,2,4-trioxanes with high in vitro antimalarial activities

Bioorg Med Chem Lett. 2005 Feb 1;15(3):595-7. doi: 10.1016/j.bmcl.2004.11.043.

Abstract

A remarkable increase in antimalarial in vitro activity was achieved by integration of spiroadamantane motifs in 6-alkylidene 1,2,4-trioxanes 3a-h via diastereoselective photooxygenation of allylic alcohols and subsequent BF(3)-catalyzed peroxyacetalization with adamantanone to give the active compounds 3e-h.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adamantane / chemistry
  • Animals
  • Antimalarials / chemical synthesis*
  • Antimalarials / pharmacology
  • Cell Death / drug effects
  • Cell Line
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Plasmodium falciparum / drug effects
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / pharmacology
  • Structure-Activity Relationship

Substances

  • Antimalarials
  • Heterocyclic Compounds
  • Spiro Compounds
  • s-trioxane
  • Adamantane