Synthesis of 4-hydroxycoumarin and 2,4-quinolinediol derivatives and evaluation of their effects on the viability of HepG2 cells and human hepatocytes culture

Eur J Med Chem. 2004 Nov;39(11):931-7. doi: 10.1016/j.ejmech.2004.07.006.

Abstract

We report here the synthesis of aromatic coumarins and aromatic alpha-quinolones which were evaluated in vitro for their protective potentialities against tert-butyl hydroperoxide (t-BHP)-induced oxidative damage on human liver cell death, i.e., human hepatoma HepG2 cell line and human hepatocytes in primary culture. We found that the presence of a benzylidene at the 3-position or a heterocycle with N and S heteroatoms on the benzopyrone or quinolone system was essential for the protective effect of these compounds against t-BHP-induced decrease in viability of cells. We found also that a methoxy group on the aromatic ring systems decreased this potential. t-BHP-induced cytotoxicity in primary cultures of human hepatocytes could be therefore prevented by these compounds suggesting that they could display hepatoprotective effects in humans.

MeSH terms

  • 4-Hydroxycoumarins / chemical synthesis*
  • 4-Hydroxycoumarins / pharmacology
  • Carcinoma, Hepatocellular / drug therapy*
  • Cell Survival / drug effects*
  • Cells, Cultured
  • Hepatocytes / drug effects*
  • Humans
  • Liver Neoplasms / drug therapy*
  • Oxidative Stress / drug effects*
  • Protective Agents / chemical synthesis
  • Protective Agents / pharmacology
  • Quinolines / chemical synthesis*
  • Quinolines / pharmacology
  • tert-Butylhydroperoxide / adverse effects

Substances

  • 4-Hydroxycoumarins
  • Protective Agents
  • Quinolines
  • tert-Butylhydroperoxide
  • 4-hydroxycoumarin