Enantiomeric resolution of novel aryloxyaminopropanol derivatives with P-adrenoceptor antagonist activity on a derivatised amylose chiral stationary phase

TY - JOUR

T1 - Enantiomeric resolution of novel aryloxyaminopropanol derivatives with P-adrenoceptor antagonist activity on a derivatised amylose chiral stationary phase

AU - Valentova, J

AU - Cizmarikova, R

AU - Bui, T T T

AU - Drake, A F

AU - Hutt, A J

PY - 2003

Y1 - 2003

N2 - The chromatographic retention and resolution of the enantiomers of a novel series of aryl-oxyaminopropanol derivatives with beta-adrenoceptor antagonist activity have been investigated using a Chiralpak AD CSP. The influence of mobile phase composition, particularly alcohol modifier content and composition, on analyte retention and separation were determined; the final composition being hexane: ethanol: methanol:diethylamine (85:3.75:11.25:0.1% by Volume). Analyte structure, including the position and nature of the aromatic substituents, steric bulk of the nitrogen alkyl substituent and length and bulk of the side chain were found to influence both retention and chiral discrimination. Semi-preparative isolation of the enantiomers of two of the compounds, followed by CD analysis of complexes formed on reaction with molybdenum tetraocetate, indicated that the enantiomeric elution order for both compounds was the same as that of propronolol, i.e. R- before S-.

AB - The chromatographic retention and resolution of the enantiomers of a novel series of aryl-oxyaminopropanol derivatives with beta-adrenoceptor antagonist activity have been investigated using a Chiralpak AD CSP. The influence of mobile phase composition, particularly alcohol modifier content and composition, on analyte retention and separation were determined; the final composition being hexane: ethanol: methanol:diethylamine (85:3.75:11.25:0.1% by Volume). Analyte structure, including the position and nature of the aromatic substituents, steric bulk of the nitrogen alkyl substituent and length and bulk of the side chain were found to influence both retention and chiral discrimination. Semi-preparative isolation of the enantiomers of two of the compounds, followed by CD analysis of complexes formed on reaction with molybdenum tetraocetate, indicated that the enantiomeric elution order for both compounds was the same as that of propronolol, i.e. R- before S-.

U2 - 10.1365/s10337-003-0114-7

DO - 10.1365/s10337-003-0114-7

M3 - Article

VL - 58

SP - 733

EP - 740

JO - CHROMATOGRAPHIA

JF - CHROMATOGRAPHIA

IS - 11-12

ER -