Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors.
This paper reports the synthesis and evaluation of the biological affinity towards benzodiazepine and A(1) and A(2A) adenosine receptors of some 3-ethoxycarbonyl or 3-phenyl-substituted 1,2, 3-triazolo[1,5-a]quinazolines. Starting from the appropriate chloro-substituted phenylazides, the series of 7 or 8 chloro-substituted triazoloquinazolines were prepared. Nitration reactions of the triazoloquinazoline ring and chlorination reactions of the hydroxyl group in the 5 position of the same ring are also reported. By nucleophilic displacement of halogen, the corresponding 5-amino derivatives and some analogous derivatives bearing cyclohexylamino and p-toluidino substituents were obtained. The binding assays showed a generalized decrease in the affinity towards the benzodiazepine receptors and confirmed a moderate affinity towards the A(1) adenosine receptors in comparison with the previously studied triazoloquinazoline derivatives.
Bertelli
L
L
Dipartimento di Scienze Farmaceutiche, Università di Pisa, Via Bonanno 6, 56126, Pisa, Italy.
Biagi
G
G
Giorgi
I
I
Livi
O
O
Manera
C
C
Scartoni
V
V
Lucacchini
A
A
Giannaccini
G
G
Barili
P L
PL
D000818:Animals; D001667:Binding, Competitive / Q000187:drug effects; D002417:Cattle; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D066298:In Vitro Techniques; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D017072:Neostriatum / Q000187:drug effects / Q000378:metabolism; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology; D043705:Receptor, Adenosine A2A; D011963:Receptors, GABA-A / Q000187:drug effects*; D018047:Receptors, Purinergic P1 / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D008024:Ligands; D011799:Quinazolines; D043705:Receptor, Adenosine A2A; D011963:Receptors, GABA-A; D018047:Receptors, Purinergic P1; D014230:Triazoles