1,2,3-Triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors

• Published in: European journal of medicinal chemistry Vol. 33; no. 2; pp. 113 - 122
• Main Authors: Bertelli, Lucia, Biagi, Giuliana, Giorgi, Irene, Manera, Clementina, Livi, Oreste, Scartoni, Valerio, Betti, Laura, Giannaccini, Gino, Trincavelli, Letizia, Barili, Pier Luigi
• Format: Journal Article
• Language: English
• Published: PARIS CEDEX 15 Elsevier Masson SAS 01.02.1998; Elsevier
• Subjects: 1,2,3-triazolo[1,5-a]quinoxalines; adenosine receptor binding; benzodiazepine receptor binding; Biological and medical sciences; Chemistry, Medicinal; Life Sciences & Biomedicine; Medical sciences; Neuropharmacology; Neurotransmitters. Neurotransmission. Receptors; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Science & Technology; benzodiazepine receptor binding; adenosine receptor binding; 1,2,3-triazolo[1,5-a]quinoxalines; THEORETICAL CALCULATIONS; A; AFFINITY; 1,2,3-TRIAZOLE<4,5-D>PYRIDAZINES; BIS-AZOLO<A,C>-FUSED QUINOXALINES; 4-AMINO DERIVATIVES; 4-SUBSTITUTED 1,2,3-TRIAZOLO<1,5-A>QUINOXALINES; Bovine; Angular nitrogen heterocycle; Ligand; Central nervous system; Lactam; A1 Adenosine receptor; Benzodiazepine receptor; Tricyclic compound; In vitro; Vertebrata; Biological fixation; Mammalia; Structure activity relation; Animal; Affinity; Aromatic compound; Artiodactyla; Chemical synthesis; Ungulata; Brain (vertebrata)
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/S0223-5234(98)80036-6

This paper reports the synthesis and binding assays toward benzodiazepine and adenosine A 1 and A 2A receptors of new 1,2,3-triazolo[1,5-a]quinoxalin-4-one derivatives. The prepared compounds show good affinity toward the benzodiazepine receptor ( K i 53–314 nM); the GABA ratio values suggest an inverse agonist activity for the N(5) unsubstituted compounds 6b-d and an agonist activity for the N(5) methylated compounds 7a-c. Some derivatives of both series show good affinity ( K i < 100 nM) and selectivity toward the adenosine A 1 receptorial subtype.