Several 9-benzyl-N6-cycloalkyl-2-phenyladenines, 9-benzyl-N6-cycloalkyl-2-phenyl-8-azaadenines and 4-cycloalkylamino-1-benzyl-6-phenyl-1H-1,2,3-triazolo[4,5-c]pyridines were prepared and assayed as A1 adenosine receptor ligands. The 1H-1,2,3-triazolo[4,5-c]pyridines were obtained starting from N,N-diethyl-1-benzyl-4-carboxyamido-5-methyl-1H-1,2,3-triazole by lithiation in anhydrous tetrahydrofurane in the presence of benzonitrile. The usual work up afforded the isolation of 1-benzyl-6-phenyl-1H-1,2,3-triazolo[4,5-c]pyridin-4-one which was treated with phosphorous oxychloride and cycloalkylamines. Some compounds showed high affinity and selectivity and the trend of Ki values corresponds to the series of 9-benzyl-N6-cycloalkyl-2-phenyladenines and 9-benzyl-N6-cycloalkyl-2-phenyl-8-azaadenines, therefore they can be considered bioisosteres. The affinity data permitted us to ascertain the role and the importance of the N(3) in the adenine or 8-azaadenine moiety in the receptor binding and to study the dimension of the receptor lipophilic pocket which is filled by the N6 substituent of adenosine derivatives.
|Autori interni:||GIORGI, IRENE|
|Autori:||BIAGI G;GIORGI I; O.LIVI; A.NARDI; F.PACCHINI; V.SCARTONI; LUCACCHINI A.|
|Titolo:||N(6)CYCLOALKYL-2-PHENYL-3-DEAZA-8-AZAADENINES: A NEW CLASS OF A1ADENOSINE RECEPTOR LIGANDS. A COMPARISON WITH THE CORRESPONDING ADENINES AND 8-AZAADENINES|
|Anno del prodotto:||2003|
|Digital Object Identifier (DOI):||10.1016/j.ejmech.2003.09.003|
|Appare nelle tipologie:||1.1 Articolo in rivista|