Bifunctional aryloxyphosphoramidate prodrugs of 2'-C-Me-uridine: synthesis and anti-HCV activity

Org Biomol Chem. 2016 Sep 21;14(37):8743-8757. doi: 10.1039/c6ob01189f.

Abstract

In an attempt to identify novel nucleoside phosphoramidate analogues for improving the anti-HCV activity of 2'-C-Me-uridine, we have synthesized for the first time a series of l-glutamic acid, l-serine, l-threonine and l-tyrosine containing aryloxyphosphoramidate prodrugs of 2'-C-Me-uridine. Evaluation of their activity against HCV revealed that they displayed very potent anti-HCV activity, with EC50 values that are in the same range as of Sofosbuvir.

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry
  • Amides / metabolism
  • Amides / pharmacology
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / metabolism
  • Antiviral Agents / pharmacology*
  • Chemistry Techniques, Synthetic
  • Hepacivirus / drug effects*
  • Hepacivirus / physiology
  • Hepatitis C / drug therapy
  • Hepatitis C / virology
  • Humans
  • Microsomes, Liver / metabolism
  • Phosphoric Acids / chemical synthesis
  • Phosphoric Acids / chemistry
  • Phosphoric Acids / metabolism
  • Phosphoric Acids / pharmacology
  • Prodrugs / chemical synthesis
  • Prodrugs / chemistry*
  • Prodrugs / metabolism
  • Prodrugs / pharmacology*
  • Uridine / analogs & derivatives*
  • Uridine / chemical synthesis
  • Uridine / chemistry
  • Uridine / metabolism
  • Uridine / pharmacology
  • Virus Replication / drug effects

Substances

  • Amides
  • Antiviral Agents
  • Phosphoric Acids
  • Prodrugs
  • O(4)-methyluridine
  • phosphoramidic acid
  • Uridine