Synthesis and adenosine receptor affinity of 7-beta-D-ribofuranosylxanthine

Nucleosides Nucleotides. 1998 Apr;17(4):759-68. doi: 10.1080/07328319808004673.

Abstract

7-beta-D-Ribofuranosylxanthine, a previously unreported isomer of xanthosine, was prepared in four steps from 7-benzylxanthine. The procedure, which involves the use of pivaloyloxymethyl groups to protect the xanthine ring, was also applied to preparation of some 1-N-alkyl derivatives of 7-ribosylxanthine. Adenosine receptor affinity for these compounds was determined. 7-beta-D-Ribofuranosylxanthine was found to have higher affinity and greater selectivity for the A1 receptor than previously reported xanthine nucleosides, and to be a partial agonist.

MeSH terms

  • Animals
  • Cerebral Cortex / metabolism
  • GTP-Binding Proteins / metabolism
  • Guanine Nucleotides / metabolism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Protein Binding
  • Purinergic P1 Receptor Agonists
  • Rats
  • Receptors, Purinergic P1 / metabolism*
  • Ribonucleosides / chemical synthesis*
  • Ribonucleosides / metabolism*
  • Xanthines

Substances

  • Guanine Nucleotides
  • Purinergic P1 Receptor Agonists
  • Receptors, Purinergic P1
  • Ribonucleosides
  • Xanthines
  • xanthosine
  • GTP-Binding Proteins