Phenyl-substituted N6-phenyladenosines and N6-phenyl-5′-N-ethylcarboxamidoadenosines with high activity at human adenosine A2B receptors

✍ Scribed by Maarten de Zwart; Miriam de Groote; Pieter A.M. van der Klein; Stephanie van Dun; Robert Bronsing; Jacobien K. von Frijtag Drabbe Künzel; Ad P. Ijzerman

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 187 KB
• Volume: 49
• Category: Article
• ISSN: 0272-4391
• DOI: 10.1002/(sici)1098-2299(200002)49:2<85::aid-ddr2>3.0.co;2-w

✦ Synopsis

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 6phenyladenosine, 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.