N6-phenyladenosines: pronounced effect of phenyl substituents on affinity for A2 adenosine receptors.
A number of N6-phenyladenosines with various substitutions on the phenyl ring have been synthesized and tested for their affinities toward brain A1 and A2 adenosine receptors. Compounds with meta substituents, such as (m-hydroxy- and m-iodophenyl)adenosine, were found to have high A1 selectivity. Meta substitution caused a selective decrease in the affinity of these compounds for A2 receptors. The results suggest that, in contrast to what is commonly held, certain N6-substituents have pronounced effects on affinity for brain A2 adenosine receptors. Thus, brain A2 receptors may have a well-defined region that recognizes N6-substitutions.
D000241:Adenosine / Q000031:analogs & derivatives* / Q000378:metabolism; D000818:Animals; D001921:Brain / Q000378:metabolism*; D002462:Cell Membrane / Q000378:metabolism; D002531:Cerebellum / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D002645:Chickens; D003342:Corpus Striatum / Q000378:metabolism; D051381:Rats; D011983:Receptors, Purinergic / Q000378:metabolism*; D013329:Structure-Activity Relationship
D011983:Receptors, Purinergic; D000241:Adenosine