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Enantiomeric separation of substituted 2-arylindoles on derivatised polysaccharide chiral stationary phases

Journal of Biochemical and Biophysical Methods
Publication Date
DOI: 10.1016/s0165-022x(02)00121-5
  • Enantiomer Separation
  • Arylindole
  • Polysaccharide Stationary Phase


Abstract The enantiomeric separation of a series of 2-arylindoles, developed as 5HT 2A receptor antagonists for the treatment of schizophrenia, was investigated. Evaluation of a number of chiral stationary phases (CSPs) suggested that Chiralcel OD-H and Chiralpak AD were the most versatile for these compounds, and were employed for more detailed studies. A degree of complementarity between the CSPs was observed, such that Chiralcel OD-H was more effective for piperidine-containing molecules and Chiralpak AD for piperazine- and morpholine-containing molecules. The presence of a basic secondary amine was detrimental chromatographically, but resolution was improved substantially by employing diethylamine (DEA) in the mobile phase. All separations were either enthalpy-controlled or showed no temperature dependence. Differential temperature effects between series highlighted the possibility of multiple binding modes on these CSPs. Based on this study, it is possible to make a more rational selection of chromatographic conditions for future novel analogues.

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