Synthesis of a series of caffeic acid phenethyl amide (CAPA) fluorinated derivatives: comparison of cytoprotective effects to caffeic acid phenethyl ester (CAPE)

Bioorg Med Chem. 2010 Jul 15;18(14):5032-8. doi: 10.1016/j.bmc.2010.05.080. Epub 2010 Jun 11.

Abstract

A series of catechol ring-fluorinated derivatives of caffeic acid phenethyl amide (CAPA) were synthesized and screened for cytoprotective activity against H2O2 induced oxidative stress in human umbilical vein endothelial cells (HUVEC). CAPA and three fluorinated analogs were found to be significantly cytoprotective when compared to control, with no significant difference in cytoprotection between caffeic acid phenethyl ester (CAPE) and CAPA.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Caffeic Acids / chemical synthesis
  • Caffeic Acids / pharmacology*
  • Cell Line
  • Cytoprotection / drug effects*
  • Halogenation
  • Humans
  • Hydrogen Peroxide / metabolism
  • Oxidative Stress / drug effects
  • Phenethylamines / chemical synthesis
  • Phenethylamines / pharmacology*
  • Phenylethyl Alcohol / analogs & derivatives*
  • Phenylethyl Alcohol / pharmacology
  • Umbilical Veins / cytology

Substances

  • Caffeic Acids
  • Phenethylamines
  • Hydrogen Peroxide
  • caffeic acid phenethyl ester
  • Phenylethyl Alcohol