Effect of functional group polarity on the antimalarial activity of spiro and dispiro-1,2,4-trioxolanes

Bioorg Med Chem. 2006 Sep 15;14(18):6368-82. doi: 10.1016/j.bmc.2006.05.041. Epub 2006 Jun 8.

Abstract

Based on the structures of several lipophilic trioxolane antimalarial prototypes, we set out to determine which functional groups were associated with good antimalarial profiles and identify more polar (lower LogP/LogD) lead compounds with good physicochemical properties. More lipophilic trioxolanes tended to have better oral activities than their more polar counterparts. Trioxolanes with a wide range of neutral and basic, but not acidic, functional groups had good antimalarial profiles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / chemical synthesis
  • Antimalarials / chemistry
  • Antimalarials / pharmacology*
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / pharmacology*
  • In Vitro Techniques
  • Molecular Conformation
  • Parasitic Sensitivity Tests
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 1,2,4-trioxane
  • Antimalarials
  • Heterocyclic Compounds
  • Spiro Compounds