Synthesis of a new family of acyclic nucleoside phosphonates, analogues of TPases transition states

Org Biomol Chem. 2012 May 7;10(17):3448-54. doi: 10.1039/c2ob25131k. Epub 2012 Mar 21.

Abstract

A 6-step procedure was developed for the synthesis of a new family of acyclic nucleoside phosphonates (ANPs), "PHEEPA" [(2-pyrimidinyl-2-(2-hydroxyethoxy)ethyl)phosphonic acids] in overall yields ranging from 4.5% to 32%. These compounds, which possess on one side a hydroxy function and on the other side a phosphonate group, can be considered either as potential antiviral agents or as transition state analogues of nucleoside phosphorylases such as thymidine phosphorylase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomimetic Materials / chemical synthesis*
  • Biomimetic Materials / chemistry*
  • Chemistry Techniques, Synthetic / methods*
  • Nucleosides / chemistry*
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry*
  • Thymidine Phosphorylase / chemistry*

Substances

  • Nucleosides
  • Organophosphonates
  • Pyrimidines
  • Thymidine Phosphorylase