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N6-cycloalkyl-2-phenyl-3-deaza-8-azaadenines: a new class of A1 adenosine receptor ligands. A comparison with the corresponding adenines and 8-azaadenines.

Abstract：

: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 N3 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.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Biagi G,Giorgi I,Livi O,Nardi A,Pacchini F,Scartoni V,Lucacchini A

doi

10.1016/j.ejmech.2003.09.003

subject

Has Abstract

pub_date

2003-11-01 00:00:00

pages

983-90

issue

11-12

eissn

0223-5234

issn

1768-3254

pii

S0223523403001831

journal_volume

38

pub_type

杂志文章

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