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Fluorenone 1,4-dihydropyridine derivatives with cardiodepressant activity: Enantiomeric separation by chiral HPLC and conformational aspects
Authors:Salvatore Caccamese  Rosa Chillemi  Grazia Principato
Abstract:The direct HPLC enantiomeric separation of five fluorenone-1,4-dihydropyridine-3,5-dicarboxylic diesters has been achieved using a Chiralpak AD stationary phase obtaining simultaneously good enantioselectivities, resolution factors, and elution times. CD spectra of the individual enantiomers for two compounds were measured. Thermodynamic parameters associated with the adsorption equilibria of the enantiomers with the chiral stationary phase were obtained from HPLC runs at various temperatures. The conformational preferences of the synperiplanar fluorenone group and of the cis/cis ester groups were obtained by 1H NMR spectra, including NOE experiments. © 1996 Wiley-Liss, Inc.
Keywords:chiral stationary phases  Chiralpak AD  CD spectra  entropy  enthalpy  1H NMR spectra  synperiplanar conformer of dihydropyridines
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