Synthetic pseudopterosin analogues: A novel class of antiinflammatory drug candidates.

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.

• Authors: Felix Flachsmann, Kurt Schellhaas, Claudia E Moya, Robert S Jacobs, William Fenical
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 18 Issue 23 Pg. 8324-33 (Dec 01 2010) ISSN: 1464-3391 [Electronic] England
• PMID: 21041093 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2010 Elsevier Ltd. All rights reserved.

Chemical References

• 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

Topics

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