Fluorenone 1,4-dihydropyridine derivatives with cardiodepressant activity: Enantiomeric separation by chiral HPLC and conformational aspects

✍ Scribed by Salvatore Caccamese; Rosa Chillemi; Grazia Principato

• Book ID: 102660315
• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 698 KB
• Volume: 8
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1996)8:3<281::aid-chir8>3.0.co;2-k

✦ Synopsis

The direct HPLC enantiomeric separation of five fluorenone-l,4dihydropyridine-3,5dicarboxylic 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 'H NMR spectra, including NOE experiments.