Premium
Phenyl‐substituted N 6 ‐phenyladenosines and N 6 ‐phenyl‐5′‐ N ‐ethylcarboxamidoadenosines with high activity at human adenosine A 2B receptors
Author(s) -
de Zwart Maarten,
de Groote Miriam,
van der Klein Pieter A.M.,
van Dun Stephanie,
Bronsing Robert,
von Frijtag Drabbe Künzel Jacobien K.,
Ijzerman Ad P.
Publication year - 2000
Publication title -
drug development research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.582
H-Index - 60
eISSN - 1098-2299
pISSN - 0272-4391
DOI - 10.1002/(sici)1098-2299(200002)49:2<85::aid-ddr2>3.0.co;2-w
Subject(s) - adenosine , adenosine receptor , pharmacology , chemistry , receptor , stereochemistry , biochemistry , medicine , agonist
A series of phenyl‐substituted N 6 ‐phenyladenosines and N 6 ‐phenyl‐5′‐ N ‐ethylcarboxamidoadenosines were synthesized and tested at adenosine receptor subtypes. EC 50 values were determined for cyclic AMP production in CHO cells expressing human A 2B receptors. Binding affinities were determined for rat A 1 and A 2A receptors and human A 3 receptors. N 6 ‐phenyladenosine displayed an EC 50 value at A 2B receptors of 6.3 μM. Several N 6 ‐phenyladenosine derivatives were more active than N 6 ‐phenyladenosine, while two analogs were also more potent than 5′‐ N ‐ethylcarboxamidoadenosine (NECA, 0.76 μM), i.e., the 4‐iodophenyl ( 10 , 0.37 μM) and the 4‐aminosulfonylphenyl ( 20 , 0.44 μM) derivatives. N 6 ‐phenyl‐NECA derivatives were as active as their analogous adenosine derivatives. Drug Dev. Res. 49:85–93, 2000. © 2000 Wiley‐Liss, Inc.