By G. Hasko, et al.,
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Additional info for Adenosine Receptors - Theraputic Aspects
The phenyl carbamoyl pharmacophores used previously in pyrazolotriazolopyrimidienes were incorporated into the N6-position of an 8-azaadenine template, of which derivatives have demonstrated selective A1AR antagonistic behavior. 63 An alternate approach to designing A3 antagonists is to start with high-affinity adenosine derivatives and simply truncate the molecule in stages to remove its ability to activate the receptor without losing its high affinity of binding. , substituted benzyl groups or large cycloalkyl rings) reduced the maximal efficacy, leading to reduced efficacy at the A3AR.
Generally, these 2-substituted adenosine derivatives were less potent at the A1AR in comparison to the A3AR, but fully efficacious at that subtype, with binding Ki values over 100 nM. The 2-phenylethyl moiety resulted in higher A3AR affinity (Ki in nM) when linked to the 2-position of adenosine through an ether group (54) than when linked through an amine (310) or thioether (>10,000). Typically, 2-ethers of adenosine are A2A-selective agonists; thus, the compounds mentioned earlier are somewhat exceptional.
G. , Pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine derivatives as highly potent and selective human A3 adenosine receptor antagonists: influence of the chain at the N8 pyrazole nitrogen, J. Med. , 43, 4768, 2000. 45. G. , Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives as highly potent and selective human A3 adenosine receptor antagonists, J. Med. , 42, 4473, 1999. 46. G. , Synthesis and preliminary biological evaluation of [3H]-MRE 3008-F20: the first high affinity radioligand antagonist for the human A3 adenosine receptors, Bioorg.