New 1,2,3-triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors. II.
On pursuing research about 1,2,3-triazolo[1,5-a]quinoxalines, in this paper we report synthesis and binding assays toward the benzodiazepine and A(1) and A(2A) adenosine receptors, of a new series of derivatives, bearing some structural changes (introduction of fluorine and trifluoromethyl in the seventh position, amino substituents in the fourth position, benzyl group in the fifth position and aroyl substituents in the third position). The biological tests have shown that only the 7-fluorosubstituted compounds 3a and 4a and the N-benzyl derivative 7 have a good affinity toward the benzodiazepine receptors, while only the 7-trifluoromethyl substituted compound 3b presents a moderate affinity with low selectivity toward the A(1) adenosine receptors. The other structural modifications strongly decreased biological activity.
Biagi
Giuliana
G
Dipartimento di Scienze Farmaceutiche, Università di Pisa, Via Bonanno, 6-56126, Pisa, Italy.
Giorgi
Irene
I
Livi
Oreste
O
Scartoni
Valerio
V
Betti
Laura
L
Giannaccini
Gino
G
Trincavelli
Maria Letizia
ML
D000818:Animals; D001923:Brain Chemistry; D002417:Cattle; D058787:GABA-A Receptor Antagonists; D008024:Ligands; D058915:Purinergic P1 Receptor Antagonists; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000378:metabolism; D011869:Radioligand Assay; D043705:Receptor, Adenosine A2A; D011963:Receptors, GABA-A / Q000378:metabolism*; D018047:Receptors, Purinergic P1 / Q000378:metabolism*; D013329:Structure-Activity Relationship
D058787:GABA-A Receptor Antagonists; D008024:Ligands; D058915:Purinergic P1 Receptor Antagonists; D011810:Quinoxalines; D043705:Receptor, Adenosine A2A; D011963:Receptors, GABA-A; D018047:Receptors, Purinergic P1