Synthesis and antiviral activity evaluation of acyclic 2'-azanucleosides bearing a phosphonomethoxy function in the side chain

Bioorg Med Chem. 2009 Jun 1;17(11):3756-62. doi: 10.1016/j.bmc.2009.04.054. Epub 2009 May 3.

Abstract

Acyclic 2'-azanucleosides with a phosphonomethoxy function in the side chain were obtained by coupling of diethyl {2-[N-(pivaloyloxymethyl)-N-(p-toluenesulfonyl)amino]ethoxymethyl}phosphonate with the pyrimidine nucleobases via the Vorbrüggen-type protocol. The compounds were evaluated in vitro for activity against a broad variety of RNA and DNA viruses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids, Acyclic / chemical synthesis
  • Acids, Acyclic / chemistry*
  • Acids, Acyclic / pharmacology
  • Adenine / analogs & derivatives
  • Adenine / chemistry
  • Adenine / pharmacology
  • Antiviral Agents* / chemical synthesis
  • Antiviral Agents* / chemistry
  • Antiviral Agents* / pharmacology
  • Aza Compounds* / chemical synthesis
  • Aza Compounds* / chemistry
  • Aza Compounds* / pharmacology
  • Cidofovir
  • Cytosine / analogs & derivatives
  • Cytosine / chemistry
  • Cytosine / pharmacology
  • DNA Viruses / drug effects*
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Nucleosides / chemical synthesis
  • Nucleosides / chemistry*
  • Nucleosides / pharmacology
  • Organophosphonates / chemical synthesis
  • Organophosphonates / chemistry*
  • Organophosphonates / pharmacology
  • RNA Viruses / drug effects*
  • Tenofovir

Substances

  • Acids, Acyclic
  • Antiviral Agents
  • Aza Compounds
  • Nucleosides
  • Organophosphonates
  • adefovir
  • Cytosine
  • Tenofovir
  • Adenine
  • Cidofovir