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Chiral Resolution of the Enantiomers of New Aromatase Inhibitors by Liquid Chromatography on Amylose Stationary Phases

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Abstract

Analytical HPLC methods for derivatized amylose chiral stationary phases were developed for the direct enantioseparation of substituted [1-(imidazo-1-yl)-1-phenylmethyl)] benzothiazolinone and benzoxazolinone derivatives with one stereogenic center. These analogues of fadrozole constitute new potent nonsteroidal inhibitors of aromatase (P450 arom.). The separations were made using normal phase methodology with mobile phase consisting of n-hexane-alcohol (ethanol, 1-propanol or 2-propanol) in various proportions, and a silica-based amylose tris-3,5-dimethylphenylcarbamate (Chiralpak AD), or tris-(S)-1-phenylethylcarbamate (Chiralpak AS). The effects of concentration of various aliphatic alcohols in the mobile phase were studied. Baseline separation (R s > 1.5) was easily obtained in all cases, ethanol being often the more interesting modifier. The effects of structural features of the solutes along with the temperature of the column on the discrimination between the enantiomers were examined for different mobile phase compositions.

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Authors and Affiliations

  1. Laboratoire de Chimie Analytique EA 1043, Faculté des Sciences Pharmaceutiques et Biologiques Université de Lille, 2 BP 83 3, rue du Pr. Laguesse, 59006, Lille Cedex, France

    C. Danel, C. Foulon, J-P. Bonte & C. Vaccher

  2. Laboratoire de Chimie Thérapeutique EA 1043, Faculté des Sciences Pharmaceutiques et Biologiques, Université de Lille 2 BP 83 3, rue du Pr. Laguesse, 59006, Lille Cedex, France

    C. Park & S. Yous

Authors
  1. C. Danel
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  2. C. Foulon
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  3. C. Park
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  4. S. Yous
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  5. J-P. Bonte
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  6. C. Vaccher
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Correspondence to C. Vaccher.

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Danel, C., Foulon, C., Park, C. et al. Chiral Resolution of the Enantiomers of New Aromatase Inhibitors by Liquid Chromatography on Amylose Stationary Phases. Chromatographia 59, 181–188 (2004). https://doi.org/10.1365/s10337-003-0167-7

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  • DOI: https://doi.org/10.1365/s10337-003-0167-7

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