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Fluorenone 1,4-dihydropyridine derivatives with cardiodepressant activity: enantiomeric separation by chiral HPLC and
S Caccamese1, R Chillemi, G Principato
1Dipartimento di Scienze Chimiche, Università di Catania, Italy.
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 HLPC 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.