title: Preparative enantiomeric separation of new selective CB2 receptor agonists by liquid chromatography on polysaccharide-based chiral stationary phases: determination of enantiomeric purity and assignment of absolute stereochemistry by X-ray structure analysis.
abstract: The development of high-performance liquid chromatography (HPLC) methods using derivatized amylose chiral stationary phases has permitted preparative enantioseparations of substituted 4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives with satisfactory yields. These compounds constitute new potent selective agonists of the cannabinoid CB(2) receptor. Analytical enantioseparation methods using UV detection were validated to determine the enantiomeric purity of these compounds. Linear calibration curves in the range from 0.18 to 0.40 mM were obtained; repeatability, limits of detection (LOD), and quantification (LOQ) were determined: LOD varied, for the various solutes, from 0.5 to 1.2 μM. All the separated compounds were prepared with high enantiomeric purities superior to 99.3% Absolute configuration of the enantiomers was unequivocally established by single crystal X-ray diffraction method and correlated to the chiroptical properties of isolated enantiomers.
authors: University of Lille Nord de France, F-59000, Lille, France.
authors: Eric
authors: E
authors: Stern
authors: Laurence
authors: L
authors: Goossens
authors: Pascal
authors: P
authors: Retailleau
authors: Brice
authors: B
authors: Kauffmann
authors: Jean-Paul
authors: JP
authors: Bonte
authors: Patrick
authors: P
authors: Depreux
authors: Jean-Francois
authors: JF
authors: Goossens
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002942:Circular Dichroism; D008968:Molecular Conformation; D011134:Polysaccharides / Q000737:chemistry; D043885:Receptor, Cannabinoid, CB2 / Q000819:agonists*; D013237:Stereoisomerism; D014961:X-Ray Diffraction / Q000379:methods*
chemical_list: D011134:Polysaccharides; D043885:Receptor, Cannabinoid, CB2