Substituted tetrahydrocarbazoles with potent activity against human papillomaviruses

Bioorg Med Chem Lett. 2009 Jul 1;19(13):3489-92. doi: 10.1016/j.bmcl.2009.05.003. Epub 2009 May 7.

Abstract

The synthesis and SAR of a series of substituted 1-aminotetrahydrocarbazoles with potent activity against human papillomaviruses are described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole are outlined and resulting changes in antiviral activity are highlighted. Several compounds with in vitro antiviral activity (W12 antiviral assay) in the low nanomolar range were identified and (1R)-6-bromo-N-[(1R)-1-phenylethyl]-2,3,4,9-tetrahydro-1H-carbazole-1-amine was selected for further evaluation.

MeSH terms

  • Animals
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacokinetics
  • Antiviral Agents / toxicity
  • Carbazoles / chemistry*
  • Carbazoles / pharmacokinetics
  • Carbazoles / toxicity
  • Cell Line
  • DNA, Viral / drug effects
  • Female
  • Humans
  • Papillomaviridae / drug effects*
  • Rats
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Carbazoles
  • DNA, Viral