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High-performance liquid chromatographic and subcritical fluid chromatographic separation of α-arylated ß-carboline, N-alkylated tetrahydroisoquinolines and their bioisosteres on polysaccharide-based chiral stationary phases.

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New, pharmacologically interesting chiral amino compounds, namely stereoisomers of α-hydroxynaphthyl-ß-carboline, benz[d]azepine and benz[c]azepine analogs as well as N-α-hydroxynaphthylbenzyl-substituted isoquinolines were enantioseparated by high-performance liquid chromatographic and subcritical fluid chromatographic (SFC)… Click to show full abstract

New, pharmacologically interesting chiral amino compounds, namely stereoisomers of α-hydroxynaphthyl-ß-carboline, benz[d]azepine and benz[c]azepine analogs as well as N-α-hydroxynaphthylbenzyl-substituted isoquinolines were enantioseparated by high-performance liquid chromatographic and subcritical fluid chromatographic (SFC) methods on polysaccharide-based chiral stationary phases. Separation of the stereoisomers was optimized in both SFC and normal phase liquid chromatographic (NP-LC) modalities by investigating the effects of the composition of the bulk solvent, temperature, and the structures of the analytes and selectors. Both NP-LC and SFC exhibited satisfactory performance, albeit with somewhat different effectiveness in the separation of the stereoisomers studied. The optimized methods offer the possibility to apply preparative-scale separations thereby enabling further pharmacological investigations of the enantiomers. This article is protected by copyright. All rights reserved.

Keywords: liquid chromatographic; separation; high performance; performance liquid

Journal Title: Journal of separation science
Year Published: 2019

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