Synthesis and purine receptor affinity of 6-oxopurine nucleosides and nucleotides containing (N)-methanocarba-pseudoribose rings.
6-Oxopurine derivatives containing a northern (N) methanocarba modification (i.e., fused cyclopropane and cyclopentane rings in place of the ribose) were synthesized and the adenosine receptor affinity measured. Guanine or hypoxanthine was coupled at the 7-position, or 1,3-dibutylxanthine was coupled at the 9-position. The pseudoribose ring was also substituted at the 5'-position with an N-methyluronamide or with phosphate groups.
Ravi
G
G
Molecular Recognition Section, LBC, NIDDK, National Institutes of Health, Bethesda, MD 20892, USA.
Lee
K
K
Ji
X
X
Kim
H S
HS
Soltysiak
K A
KA
Marquez
V E
VE
Jacobson
K A
KA
D002118:Calcium / Q000378:metabolism; D004353:Drug Evaluation, Preclinical / Q000379:methods; D006147:Guanine / Q000737:chemistry; D018922:HL-60 Cells / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D019271:Hypoxanthine / Q000737:chemistry; D009705:Nucleosides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D009711:Nucleotides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D058906:Purinergic P1 Receptor Agonists; D043705:Receptor, Adenosine A2A; D043684:Receptor, Adenosine A3; D018047:Receptors, Purinergic P1 / Q000187:drug effects / Q000378:metabolism*; D013329:Structure-Activity Relationship
D009705:Nucleosides; D009711:Nucleotides; D058906:Purinergic P1 Receptor Agonists; D043705:Receptor, Adenosine A2A; D043684:Receptor, Adenosine A3; D018047:Receptors, Purinergic P1; D019271:Hypoxanthine; D006147:Guanine; D002118:Calcium