Synthesis and in vitro anti-hepatitis B virus activity of 6H-[1]benzothiopyrano[4,3-b]quinolin-9-ols

Bioorg Med Chem. 2009 Jul 1;17(13):4569-74. doi: 10.1016/j.bmc.2009.05.001. Epub 2009 May 6.

Abstract

A series of novel 6H-[1]benzothiopyrano[4,3-b]quinoline derivatives were prepared and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in human hepatoblastoma-derived liver Hep-G2 cells. Compounds 10g, 10h, 10j, 10l and 10o were found to be potent anti-HBV compounds with IC(50) values less than 50 microM. The most promising compound was 10l, with an IC(50) value of 14.7 microM and a SI value of 12.4. This is the first report of the anti-HBV effects of 6H-[1]benzothiopyrano[4,3-b] quinolin-9-ols.

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Antiviral Agents / toxicity
  • Cell Line, Tumor
  • Cell Survival / drug effects*
  • DNA, Viral / analysis
  • DNA, Viral / metabolism
  • Hepatitis B Surface Antigens / analysis
  • Hepatitis B Surface Antigens / metabolism
  • Hepatitis B virus / drug effects*
  • Hepatitis B virus / physiology
  • Humans
  • Inhibitory Concentration 50
  • Liver / cytology
  • Microbial Sensitivity Tests
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*
  • Quinolines / pharmacology*
  • Quinolines / toxicity
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • DNA, Viral
  • Hepatitis B Surface Antigens
  • Quinolines