Comparative study between the polysaccharide-based chiralcel OJ and chiralcel OD CSPSs in chromatographic enantioseparation of imidazole analogues of fluoxetine and miconazole.
The enantiomeric separation of a series of imidazole analogues of Fluoxetine and Miconazole endowed with potent antifungal activity was performed using cellulose tris(4-methylbenzoate) (Chiralcel OJ) and cellulose tris(3,5-dimethylphenylcarbamate) (Chiralcel OD) as chiral stationary phases. Binary mixtures of n-hexane and alcohol as well as pure alcohols (ethanol or 2-propanol) were used as eluents. The enantiomer elution order was monitored by chiroptical detectors based on on-line optical rotation and circular dichroism measurements. For some of the compounds studied very high enantioseparation factor values (alpha > 7) on Chiralcel OJ CSP were observed. In order to study the chiroptical characteristics of the two most biologically active compounds, chromatographic resolutions were carried out on a semipreparative scale. Assignment of the absolute configuration was empirically established by comparing the CD spectra of the separated enantiomers with those obtained from the enantiomers of Miconazole.
Cirilli
Roberto
R
Dipartimento del Farmaco, Istituto Superiore di Sanità, Viale Regina Elena 299,1-00161 Roma, Italy.
Ferretti
Rosella
R
Gallinella
Bruno
B
La Torre
Francesco
F
La Regina
Giuseppe
G
Silvestri
Romano
R
D018687:Antidepressive Agents, Second-Generation / Q000737:chemistry*; D000935:Antifungal Agents / Q000737:chemistry*; D002482:Cellulose / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods; D002942:Circular Dichroism; D005473:Fluoxetine / Q000737:chemistry*; D008825:Miconazole / Q000737:chemistry*; D015394:Molecular Structure; D048448:Phenylcarbamates / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D013237:Stereoisomerism
D018687:Antidepressive Agents, Second-Generation; D000935:Antifungal Agents; D048448:Phenylcarbamates; D011134:Polysaccharides; D005473:Fluoxetine; C079151:cellulose trisphenylcarbamate; D008825:Miconazole; D002482:Cellulose