title: Liquid chromatographic resolution of 3-amino-1,4-benzodiazepin-2-one derivatives on various Pirkle-type chiral stationary phases.
abstract: The two enantiomers of N-acyl amide and N-ureide derivatives of 3-amino-5-phenyl-1,4-benzodiazepin-2-ones, which have been known to show anti-respiratory syncytial virus (RSV) activity, were resolved on seven different Pirkle-type chiral stationary phases (CSPs) with the use of 10% isopropyl alcohol in hexane as a mobile phase. Among the seven Pirkle-type CSPs, the one based on (S)-leucine derivative named as N-Phe-L-Leu was found to be most successful, the separation factors (α) and the resolutions (R(S) ) for seven analytes being in the range of 1.78-4.21 and 5.94-15.08, respectively. By resolving N-benzyloxycarbonyl derivatives of 3-amino-5-phenyl(or 5-methyl)-1,4-benzodiazepin-2-ones on Pirkle-type CSPs, the phenyl ring at the 5-position and the NH hydrogen at the 1-position of analytes were found to play an important role in the chiral recognition.
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, South Korea.
authors.forename: Je Young
authors.initials: JY
authors.lastname: Park
authors.forename: Hwan Sun
authors.initials: HS
authors.lastname: Cho
authors.forename: Myung Ho
authors.initials: MH
authors.lastname: Hyun
mesh_terms: D000438:Alcohols / Q000737:chemistry; D001569:Benzodiazepines / Q000737:chemistry*; D001570:Benzodiazepinones / Q000737:chemistry*; D002845:Chromatography / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D002853:Chromatography, Liquid / Q000379:methods*; D006859:Hydrogen / Q000737:chemistry; D007930:Leucine / Q000737:chemistry; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D001570:Benzodiazepinones; D001569:Benzodiazepines; D006859:Hydrogen; D007930:Leucine; D009584:Nitrogen