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Synthesis of New 2‐Phenyladenines and 2‐Phenylpteridines and Biological Evaluation as Adenosine Receptor Ligands
Author(s) -
Giorgi Irene,
Biagi Giuliana,
Livi Oreste,
Leonardi Michele,
Scartoni Valerio,
Pietra Daniele
Publication year - 2007
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200600168
Subject(s) - chemistry , adenosine , adenosine receptor , receptor , stereochemistry , substituent , affinities , pteridine , biochemistry , agonist , enzyme
Synthesis and biological assays of a series of 2‐phenylpteridine derivatives are described to compare their affinities to adenosine receptors with those of the corresponding adenines, purposely prepared, and 8‐azaadenines previously described. This study demonstrates that the enlargement of the five‐membered ring of the adenine nucleus to a six‐membered one is a modification that does not allow the molecules to maintain high activity towards adenosine receptors; in fact, pteridine derivatives did not show themselves to be good adenosine receptor ligands. On the contrary, N 6 ‐cycloalkyl‐ or N 6 ‐alkyl‐2‐phenyladenines showed a very high affinity and selectivity for A 1 adenosine receptors. We demonstrate also that the 9‐benzyl substituent is crucial for conferring high affinity for A 3 receptors to molecules having a 2‐phenyladenine‐like nucleus.