Synthesis of ferulic ester dimers, functionalisation and biological evaluation as potential antiatherogenic and antiplasmodial agents

Bioorg Med Chem. 2007 Sep 15;15(18):6018-26. doi: 10.1016/j.bmc.2007.06.047. Epub 2007 Jun 29.

Abstract

Oxidative dimerization of ferulic acid methyl ester afforded dihydrobenzofuran derivative and new linear compound identified by X-ray crystallography. The gallate derivatized dihydrobenzofuran analogue was obtained and all compounds were evaluated for potential antiatherogenic, antiplasmodial (best IC(50)=0.8 microM) and cytotoxic activities.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Atherosclerosis / drug therapy*
  • Atherosclerosis / metabolism
  • Cell Survival / drug effects*
  • Coumaric Acids / chemical synthesis*
  • Coumaric Acids / chemistry
  • Coumaric Acids / pharmacology
  • Dimerization
  • Endothelium, Vascular / cytology
  • Endothelium, Vascular / drug effects*
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Esters / pharmacology
  • Humans
  • Leukemia P388 / drug therapy
  • Leukemia P388 / metabolism
  • Leukemia P388 / pathology
  • Lipoproteins, LDL / metabolism*
  • Mice
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects*
  • Thiobarbituric Acid Reactive Substances / metabolism

Substances

  • Antioxidants
  • Coumaric Acids
  • Esters
  • Lipoproteins, LDL
  • Thiobarbituric Acid Reactive Substances
  • ferulic acid