title: Synthesis and in-vitro pharmacological evaluation of new 5-HT1A receptor ligands containing a benzotriazinone nucleus.
abstract: This paper reports the microwave-assisted synthesis and the binding assays on the 5-HT(1A), 5-HT(2A) and 5-HT(2C) receptors of new benzotriazinone derivatives, in order to identify selective ligands for the 5-HT(1A) subtype receptor. Conventional and microwave heating of the reactions were compared. Good yields and short reaction times are the main advantages of our synthetic route. More active compounds were selected and further evaluated for their binding affinities on D(1), D(2) dopaminergic and alpha(1), alpha(2) adrenergic receptors. The 3-(2-(4-(naphthalen-1-yl)piperazin-1-yl)ethyl)benzo[d][1,2,3]triazin-4(3H)-one 5 with K(i)= 0.000178 nM was the most active and selective derivative for the 5-HT(1A)receptor with respect to other serotonin receptors and the most selective derivative compared to dopaminergic and adrenergic receptors.
authors: Dipartimento di Chimica Farmaceutica e Tossicologica, Università degli Studi di Napoli Federico II, Napoli, Italy.
authors: Ferdinando
authors: F
authors: Fiorino
authors: Beatrice
authors: B
authors: Severino
authors: Francesca
authors: F
authors: De Angelis
authors: Elisa
authors: E
authors: Perissutti
authors: Francesco
authors: F
authors: Frecentese
authors: Paola
authors: P
authors: Massarelli
authors: Giancarlo
authors: G
authors: Bruni
authors: Elga
authors: E
authors: Collavoli
authors: Vincenzo
authors: V
authors: Santagada
authors: Giuseppe
authors: G
authors: Caliendo
mesh_terms: D000818:Animals; D001665:Binding Sites; D002540:Cerebral Cortex / Q000378:metabolism; D003342:Corpus Striatum / Q000378:metabolism; D066298:In Vitro Techniques; D008024:Ligands; D008297:Male; D008872:Microwaves; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011869:Radioligand Assay; D051381:Rats; D017207:Rats, Sprague-Dawley; D044282:Receptor, Serotonin, 5-HT1A / Q000378:metabolism*; D013329:Structure-Activity Relationship; D014227:Triazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: C527672:3-(2-(4-(naphthalen-1-yl)piperazin-1-yl)ethyl)benzo(d)(1,2,3)triazin-4(3H)-one; D008024:Ligands; D009281:Naphthalenes; D010879:Piperazines; D014227:Triazines; D044282:Receptor, Serotonin, 5-HT1A