Synthesis and antiviral activity of 2,4-diamino-5-cyano-6-[2-(phosphonomethoxy)ethoxy]pyrimidine and related compounds

Bioorg Med Chem. 2004 Jun 15;12(12):3197-202. doi: 10.1016/j.bmc.2004.04.002.

Abstract

Synthesis of 2,4-diamino-5-cyano-6-[[(diisopropoxyphosphoryl)methoxy]ethoxy]pyrimidine was based on the formation of the pyrimidine ring by cyclization followed by modification of the side chain by alkylation. The 5-cyano group was also transformed to a 5-formyl and 5-hydroxymethyl group by reduction. As a side product an unexpected dimer was formed. Resulting compounds were converted to the free phosphonic acids by treatment with bromotrimethylsilane followed by hydrolysis. The 5-cyano and 5-formyl derivatives showed pronounced antiretroviral activity, comparable to that of the reference drugs adefovir and tenofovir.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cell Line
  • DNA Viruses / drug effects
  • HIV / drug effects
  • Mice
  • Molecular Structure
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*

Substances

  • 2,4-diamino-5-cyano-6-(2-(phosphonomethoxy)ethoxy)pyrimidine
  • Antiviral Agents
  • Pyrimidines
  • pyrimidine