title: Synthesis of 11-aryl-5H-imidazo[2,1-c][1,4]benzodiazepines and their benzodiazepine and A1 adenosine binding activity.
abstract: In the context of a research program aimed at elucidating the properties of the 5H-imidazo[2,1-c][1.4]benzodiazepine system, a series of 11-aryl-5H-imidazo[2,1-c][1,4]benzodiazepines (3a-i) and their 10,11-dihydro-derivatives (4a-i) has been synthesized. The synthetic strategy includes the preparation of the aryl-[1-(2-nitrobenzyl)-1H-imidazol-2-yl]methanones (5a-i) followed by their reduction and subsequent cyclization. Affinities of compounds 3a-i and 4a-i for central benzodiazepine as well as for adenosine A1-receptors were determined by radioligand binding assays. Among the unsaturated analogues, the highest activity at both receptors is displayed by 1H-(2-thienyl) derivative 3e. The hydrogenated analogues 4a-i do not exhibit considerable binding affinity either for central benzodiazepine or for adenosine A1-receptors.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Trieste, Italy. facfarm@univ.trieste.it
authors.forename: S
authors.initials: S
authors.lastname: Castellano
authors.forename: L
authors.initials: L
authors.lastname: Zorzin
authors.forename: C
authors.initials: C
authors.lastname: Florio
authors.forename: F
authors.initials: F
authors.lastname: Frausin
authors.forename: G
authors.initials: G
authors.lastname: Stefancich
mesh_terms: D000818:Animals; D014151:Anti-Anxiety Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D001665:Binding Sites / Q000187:drug effects; D008297:Male; D051379:Mice; D008808:Mice, Inbred CBA; D051381:Rats; D017207:Rats, Sprague-Dawley; D018047:Receptors, Purinergic P1 / Q000378:metabolism*
chemical_list: D014151:Anti-Anxiety Agents; D018047:Receptors, Purinergic P1; D001569:Benzodiazepines