title: Enantioselective recognition of 2,3-benzodiazepin-4-one derivatives with anticonvulsant activity on several polysaccharide chiral stationary phases.
abstract: The retention behaviour of racemic 1-(4-aminophenyl)-1,2,3,5-tetrahydro-7,8-methylendioxy-4H-2,3-benzodiazepin-4-one derivatives with anticonvulsant activity on several chiral stationary phases was investigated. The selective performances of six polysaccharide phases, namely, Chiralcel OA, OD, OF, OG, OJ and Chiralpak AD were studied and normal phase HPLC methods were optimized to separate the enantiomeric forms of this class of compounds. The chiral recognition mechanism between the analytes and the chiral selectors was discussed. A molecular modeling study was carried out with the aim to explore the enantioselective molecular recognition process with the Chiralcel OG stationary phase.
authors.affiliation: Dipartimento Farmaco-Chimico, Facoltà di Farmacia, Università di Messina, Viale Annunziata, 98168 Messina, Italy. mlcalabro@pharma.unime.it
authors.forename: Maria Luisa
authors.initials: ML
authors.lastname: Calabrò
authors.forename: Daniela
authors.initials: D
authors.lastname: Raneri
authors.forename: Silvana
authors.initials: S
authors.lastname: Tommasini
authors.forename: Rita
authors.initials: R
authors.lastname: Ficarra
authors.forename: Stefano
authors.initials: S
authors.lastname: Alcaro
authors.forename: Andrea
authors.initials: A
authors.lastname: Gallelli
authors.forename: Nicola
authors.initials: N
authors.lastname: Micale
authors.forename: Maria
authors.initials: M
authors.lastname: Zappalà
authors.forename: Paola
authors.initials: P
authors.lastname: Ficarra
mesh_terms: D000688:Amylose / Q000031:analogs & derivatives / Q000737:chemistry; D000927:Anticonvulsants / Q000032:analysis* / Q000737:chemistry; D001570:Benzodiazepinones / Q000032:analysis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D008958:Models, Molecular; D008968:Molecular Conformation; D009010:Monte Carlo Method; D048448:Phenylcarbamates / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000927:Anticonvulsants; D001570:Benzodiazepinones; D048448:Phenylcarbamates; D011134:Polysaccharides; C080033:Chiralpak AD; D000688:Amylose