Synthesis AND Adenosine Receptor Affinity of 7-β-D-Ribofuranosylxanthine

7-β-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-ribosylxanth...

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Bibliographic Details
Published in:Nucleosides & nucleotides 1998-04, Vol.17 (4), p.759-768
Main Authors: Bridson, Peter K., Lin, Xu, Melman, Neli, Ji, Xiao-duo, Jacobson, Kenneth A.
Format: Article
Language:English
Subjects:
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
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Summary:7-β-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-β-D-Ribofuranosylxanthine was found to have higher affinity and greater selectivity for the A 1 receptor than previously reported xanthine nucleosides, and to be a partial agonist.
ISSN:0732-8311
DOI:10.1080/07328319808004673