title: Enantioseparation, absolute configuration determination, and anticonvulsant activity of (+/-)-1-(4-aminophenyl)-7,8-methylenedioxy-1,2,3,5-tetrahydro-4H-2,3-benzodiazepin-4-one.
abstract: The resolution of 1-(4-aminophenyl)-7,8-methylenedioxy-1,2,3,5-tetrahydro-4H-benzodiazepin-4-one (+/-)-(R,S)-2 was accomplished by chiral HPLC. The absolute configuration of (+)-2, determined by X-ray crystallographic analysis, was R. The in vivo anticonvulsant activity of the enantiomers (+)-(R)-2 and (-)-(S)-2 is reported. It has been also demonstrated that compound (+/-)-(R,S)-2 in vivo undergoes oxidative metabolism to derivative 1.
authors.affiliation: Dipartimento Farmaco-Chimico, Università di Messina, Messina, Italy.
authors.forename: Maria Luisa
authors.initials: ML
authors.lastname: Calabrò
authors.forename: Daniela
authors.initials: D
authors.lastname: Raneri
authors.forename: Paola
authors.initials: P
authors.lastname: Ficarra
authors.forename: Guido
authors.initials: G
authors.lastname: Ferreri
authors.forename: Giovambattista
authors.initials: G
authors.lastname: De Sarro
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Bruno
authors.forename: Maria
authors.initials: M
authors.lastname: Zappalà
authors.forename: Nicola
authors.initials: N
authors.lastname: Micale
authors.forename: Silvana
authors.initials: S
authors.lastname: Grasso
mesh_terms: D000818:Animals; D000927:Anticonvulsants / Q000737:chemistry* / Q000494:pharmacology; D001570:Benzodiazepinones / Q000737:chemistry* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D051381:Rats; D017207:Rats, Sprague-Dawley; D013237:Stereoisomerism
chemical_list: C516046:1-(4-aminophenyl)-7,8-methylenedioxy-1,2,3,5-tetrahydro-4H-2,3-benzodiazepin-4-one; D000927:Anticonvulsants; D001570:Benzodiazepinones