1,2,3-triazole[4,5-d]pyridazines. III--Synthesis of new 4-amino derivatives and their affinity toward adenosine receptors.
This paper describes the preparation and adenosine receptor binding of new 1-benzyl-4-aminosubstituted-1,2,3-triazole[4,5-d]pyridazines and of other 4-aminoderivatives bearing in the 1 position other neutral substituents. The synthetic procedures consist of nucleophilic displacement reactions from the 4-chloro derivative (procedure 1), of displacement of O-sililated intermediates (procedure 2) and of the use of phosphorus pentoxide-triethylamine hydrochloride reagent (procedure 3). The A1 adenosine receptor affinity is confirmed for the 1-benzyl substituted compounds bearing in the 4 position an arylamino or cycloalkylamino group. In addition, the compound obtained by reaction with racemic alpha-methylbenzylamine shows an interesting A1 activity, unlike the 4-benzylamino derivative.
Biagi
G
G
Istituto di Chimica Farmaceutica e Tossicologica, Università di Pisa.
Giorgi
I
I
Livi
O
O
Scartoni
V
V
Lucacchini
A
A
Senatore
G
G
Barili
P L
PL
D000588:Amines / Q000737:chemistry; D000818:Animals; D001667:Binding, Competitive; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011724:Pyridazines / Q000138:chemical synthesis* / Q000378:metabolism; D051381:Rats; D018047:Receptors, Purinergic P1 / Q000378:metabolism*; D012756:Sheep; D014230:Triazoles / Q000138:chemical synthesis* / Q000378:metabolism
D000588:Amines; D011724:Pyridazines; D018047:Receptors, Purinergic P1; D014230:Triazoles