Synthesis of BC-ring model of globostellatic acid X methyl ester, an anti-angiogenic substance from marine sponge

Bioorg Med Chem Lett. 2008 Jun 15;18(12):3532-5. doi: 10.1016/j.bmcl.2008.05.018. Epub 2008 May 7.

Abstract

Concise synthesis of BC-ring model compounds of 13E,17E-globostellatic acid X methyl ester, an anti-angiogenic triterpene derivative from Indonesian marine sponge, was achieved through ynolate olefination and allylic oxidation as key steps. The model compound 5, which was synthesized within 10 reaction steps from commercially available Hajos-Parrish ketone, showed anti-proliferative activity against HUVECs with moderate selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiogenesis Inhibitors / chemical synthesis*
  • Angiogenesis Inhibitors / chemistry
  • Angiogenesis Inhibitors / pharmacology
  • Animals
  • Cell Line
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Endothelial Cells / drug effects
  • Humans
  • Indonesia
  • KB Cells
  • Molecular Conformation
  • Porifera / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry
  • Triterpenes / pharmacology*

Substances

  • Angiogenesis Inhibitors
  • Triterpenes
  • globostellatic acid X methyl ester