Synthesis and adenosine receptor affinity of 7-beta-D-ribofuranosylxanthine.
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.
Chemistry Department, University of Memphis, TN 38152, USA.
P K
PK
Bridson
X
X
Lin
N
N
Melman
X D
XD
Ji
K A
KA
Jacobson
D000818:Animals; D002540:Cerebral Cortex / Q000378:metabolism; D019204:GTP-Binding Proteins / Q000378:metabolism; D006150:Guanine Nucleotides / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011485:Protein Binding; D058906:Purinergic P1 Receptor Agonists; D051381:Rats; D018047:Receptors, Purinergic P1 / Q000378:metabolism*; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000378:metabolism*; D014970:Xanthines
D006150:Guanine Nucleotides; D058906:Purinergic P1 Receptor Agonists; D018047:Receptors, Purinergic P1; D012263:Ribonucleosides; D014970:Xanthines; C005893:xanthosine; D019204:GTP-Binding Proteins