title: 1,2,3-triazole[4,5-d]pyridazines. III--Synthesis of new 4-amino derivatives and their affinity toward adenosine receptors.
abstract: 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.
authors.affiliation: Istituto di Chimica Farmaceutica e Tossicologica, Università di Pisa.
authors.forename: G
authors.initials: G
authors.lastname: Biagi
authors.forename: I
authors.initials: I
authors.lastname: Giorgi
authors.forename: O
authors.initials: O
authors.lastname: Livi
authors.forename: V
authors.initials: V
authors.lastname: Scartoni
authors.forename: A
authors.initials: A
authors.lastname: Lucacchini
authors.forename: G
authors.initials: G
authors.lastname: Senatore
authors.forename: P L
authors.initials: PL
authors.lastname: Barili
mesh_terms: 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
chemical_list: D000588:Amines; D011724:Pyridazines; D018047:Receptors, Purinergic P1; D014230:Triazoles