Synthesis and biological activity of bimorpholine and its carbanucleoside

Nucleosides Nucleotides Nucleic Acids. 2011 Nov;30(11):897-907. doi: 10.1080/15257770.2011.621919.

Abstract

A new enantiomerically pure carbacyclic nucleoside analogue with bimorpholine as a nonaromatic nucleobase was synthesized. The nucleoside analogue and bimorpholine were tested for cytotoxicity using an MTT assay and the xCELLigence System. Both assays revealed that compound 3 was highly cytotoxic at a 50 μM concentration while the cytotoxic effect of compound 1 was much less prominent. No antiretroviral activity was detected for this compound. In contrast, it acted as a potent inhibitor of hepatitis C virus (HCV) replication. Most likely this effect originates largely from the cytotoxicity of the compound; however, it is possible that a specific mechanism of HCV inhibition also exists.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Hepacivirus / drug effects*
  • Hepatitis C / drug therapy
  • Humans
  • Morpholines / chemical synthesis
  • Morpholines / chemistry*
  • Morpholines / pharmacology*
  • Nucleosides / chemical synthesis
  • Nucleosides / chemistry*
  • Nucleosides / pharmacology*
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Morpholines
  • Nucleosides