2-Phenylhydroxypropynyladenosine derivatives as high potent agonists at A2B adenosine receptor subtype.
Adenosine derivatives bearing in 2-position the (R,S)-phenylhydroxypropynyl chain were evaluated for their potency at human A2B adenosine receptor, stably transfected on CHO cells, on the basis that (R,S)-2-phenylhydroxy-propynyl-5'-N-ethylcarboxyamidoadenosine [(R,S)-PHPNECA] was found to be a good agonist at the A2B receptor subtype. Biological studies demonstrated that the presence of small alkyl groups in N6-position of these molecules are well tolerated, whereas large groups abolished A2B potency. On the other hand, the presence of an ethyl group in the 4'-carboxamido function seems to be optimal, the (S)-PHPNECA resulting the most potent agonist at A2B receptor reported so far.
Lambertucci
C
C
Dipartimento di Scienze Chimiche, University of Camerino, Camerino, Italy.
Volpini
R
R
Costanzi
S
S
Taffi
S
S
Vittori
S
S
Cristalli
G
G
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D058908:Adenosine A2 Receptor Agonists; D007202:Indicators and Reagents; D008958:Models, Molecular; D015394:Molecular Structure
C111199:2-(3-hydroxy-3-phenyl-1-propyn-1-yl)-5'-N-ethylcarboxamidoadenosine; C479243:2-Phenylhydroxypropynyladenosine; D058908:Adenosine A2 Receptor Agonists; D007202:Indicators and Reagents; D000241:Adenosine