title: Liquid Chromatographic Separation of Novel 4-Amino-Flavanes Series Diastereomers on a Polysaccharide-Type Chiral Stationary Phase.
abstract: Two broad approaches for the syntheses of a series of 4-aminoflavanes are used in this study, and they have been prepared in 30-99% overall yields using the reductive condensation of flavanone with primary amine, as a key step. By this methodology, the formyl derivatives of several secondary amines were obtained in good to excellent yields. The structures of all new products have been confirmed by spectral experiences (IR,1H NMR and13C NMR). However, the present non-stereoselective synthesis results in a mixture of 2-7: diastereomers, which differ from the configuration of the flavanone atom asymmetric center. Since each diastereomer may have different biological activity and pharmacokinetic profile, analytical methods have to be developed for their separation. The 4-aminoflavanes diastereomers were separated using polysaccharide chiral stationary phases columns consisting of cellulose (Chiralcel®OD-H and Chiralcel®OJ) by high-performance liquid chromatography; the separation was affected by the nature and concentration of the alcohol modifiers in the mobile phase. Separations were carried out under normal phase mode on the Chiralcel®OJ column. This method can properly separate the two diastereoisomers (Rs > 2) within an analysis time of <50 min.
authors.affiliation: Bioactive Molecules and Chiral Separation Laboratory, Faculty of Science and Technology, University of Bechar, Bechar, Algeria.
authors.forename: Ismahane
authors.initials: I
authors.lastname: Rahou
authors.affiliation: Bioactive Molecules and Chiral Separation Laboratory, Faculty of Science and Technology, University of Bechar, Bechar, Algeria.
authors.forename: Khaled
authors.initials: K
authors.lastname: Sekkoum
authors.affiliation: Bioactive Molecules and Chiral Separation Laboratory, Faculty of Science and Technology, University of Bechar, Bechar, Algeria.
authors.forename: Nasser
authors.initials: N
authors.lastname: Belboukhari
authors.affiliation: Phytochemistry and Organic Synthesis Laboratory, Faculty of Science and Technology, University of Bechar, Bechar, Algeria.
authors.forename: Abdelkrim
authors.initials: A
authors.lastname: Cheriti
authors.affiliation: Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Center, Dokki, Giza 12622, Egypt haboulenein@yahoo.com.
authors.forename: Hassan Y
authors.initials: HY
authors.lastname: Aboul-Enein
mesh_terms: D002482:Cellulose / Q000737:chemistry; D002623:Chemistry Techniques, Analytical / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D005419:Flavonoids / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005419:Flavonoids; D011134:Polysaccharides; C413760:aminoflavone; D002482:Cellulose