Synthetic pseudopterosin analogues: A novel class of antiinflammatory drug candidates

Bioorg Med Chem. 2010 Dec 1;18(23):8324-33. doi: 10.1016/j.bmc.2010.09.067. Epub 2010 Oct 7.

Abstract

The synthesis and in vivo anti-inflammatory activity of a series of pseudopterosin analogues are presented. Synthetic tricyclic catechol aglycons with different substitution patterns were monofucosylated or -xylosylated. Anti-inflammatory activity was conserved over a wide range of structural modifications. The most active synthetic compound 33 reduced phorbol myristate acetate (PMA)-induced inflammation in the mouse ear by 72% at 50 μg/ear. This corresponds to 80% of the activity of natural pseudopterosin A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / therapeutic use
  • Catechols / chemistry
  • Diterpenes / chemical synthesis
  • Diterpenes / chemistry*
  • Diterpenes / therapeutic use
  • Galactosides / chemical synthesis*
  • Galactosides / chemistry
  • Galactosides / therapeutic use
  • Glycosides / chemical synthesis
  • Glycosides / chemistry*
  • Glycosides / therapeutic use
  • Inflammation / chemically induced
  • Inflammation / drug therapy
  • Mice
  • Phenalenes / chemical synthesis*
  • Phenalenes / chemistry
  • Phenalenes / therapeutic use
  • Structure-Activity Relationship
  • Tetradecanoylphorbol Acetate / toxicity

Substances

  • 4-hydroxy-3,3-dimethyl-2,3,7,8,9,9a-hexahydro-1H-phenalen-5-yl 6-deoxygalactopyranoside
  • Anti-Inflammatory Agents
  • Catechols
  • Diterpenes
  • Galactosides
  • Glycosides
  • Phenalenes
  • pseudopterosins
  • catechol
  • Tetradecanoylphorbol Acetate