Synthesis and A1 and A2A adenosine binding activity of some pyrano[2,3-c]pyrazol-4-ones.
A series of pyrano[2,3-c]pyrazol-4-ones was synthesized and evaluated for bovine brain adenosine A1 and A2A receptor binding affinity. Substituents at positions 5 and/or 6 were varied in order to define the structure-activity relationships in these new kinds of adenosine receptor ligands. The most selective and potent ligand among the reported compounds was the 1,4-dihydro-1-phenyl-3-methyl-6-(3-aminophenyl)-pyrano[2,3-c]pyraz ol-4-one 11 which showed a 27-fold selectivity for A1 receptor and a Ki value of 84 nM.
Colotta
V
V
Dipartimento di Scienze Farmaceutiche, Università di Firenze, Florence, Italy.
Catarzi
D
D
Varano
F
F
Melani
F
F
Filacchioni
G
G
Cecchi
L
L
Trincavelli
L
L
Martini
C
C
Lucacchini
A
A
D000818:Animals; D002417:Cattle; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000378:metabolism; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000378:metabolism; D043705:Receptor, Adenosine A2A; D018047:Receptors, Purinergic P1 / Q000378:metabolism*
D011714:Pyrans; D011720:Pyrazoles; D043705:Receptor, Adenosine A2A; D018047:Receptors, Purinergic P1