2-Nitro analogues of adenosine and 1-deazaadenosine: synthesis and binding studies at the adenosine A1, A2A and A3 receptor subtypes.
The influence of nitro substituents on the properties of adenosine and 1-deazaadenosine was studied. Combination of a nitro group at the 2-position with several N6 substituents such as cyclopentyl and m-iodobenzyl gave a series of analogues with good adenosine receptor affinity, showing directable selectivity for the A1, A2A and A3 adenosine receptor subtypes.
Wanner
M J
MJ
Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, The Netherlands.
Von Frijtag Drabbe Künzel
J K
JK
Ijzerman
A P
AP
Koomen
G J
GJ
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism*; D000818:Animals; D001665:Binding Sites; D006801:Humans; D008024:Ligands; D011485:Protein Binding; D058906:Purinergic P1 Receptor Agonists; D011869:Radioligand Assay; D051381:Rats; D043705:Receptor, Adenosine A2A; D043684:Receptor, Adenosine A3; D018047:Receptors, Purinergic P1 / Q000378:metabolism; D014372:Tubercidin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism
D008024:Ligands; D058906:Purinergic P1 Receptor Agonists; D043705:Receptor, Adenosine A2A; D043684:Receptor, Adenosine A3; D018047:Receptors, Purinergic P1; D000241:Adenosine; D014372:Tubercidin