Design, Synthesis, and Anti-Inflammatory Activity Both in Vitro and in Vivo of New Betulinic Acid Analogues Having an Enone Functionality in Ring A

Bioorg Med Chem Lett. 2006 Dec 15;16(24):6306-9. doi: 10.1016/j.bmcl.2006.09.012. Epub 2006 Sep 25.

Abstract

Fifteen new betulinic acid analogues were designed, synthesized, and tested for anti-inflammatory activity. Many of these analogues effectively suppress nitric oxide (NO) production in RAW cells stimulated with interferon-gamma. Analogue 10 is highly and orally active in vivo for induction of the anti-inflammatory and cytoprotective enzyme, heme oxygenase-1.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Cell Line
  • Drug Design
  • Macrophages / drug effects
  • Mice
  • Models, Molecular
  • Molecular Conformation
  • Nitric Oxide / antagonists & inhibitors
  • Structure-Activity Relationship
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry
  • Triterpenes / pharmacology*

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Triterpenes
  • Nitric Oxide
  • betulinic acid