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

Attila Bajtai, Gyula Lajkó, Gábor Németi, I. Szatmári, F. Fülöp, A. Péter, I. Ilisz

Research output: Contribution to journalArticle

1 Citation (Scopus)

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 methods on polysaccharide-based chiral stationary phases. Separation of the stereoisomers was optimized in both subcritical fluid chromatography and normal phase liquid chromatographic modes by investigating the effects of the composition of the bulk solvent, temperature, and the structures of the analytes and selectors. Both normal phase liquid chromatography and subcritical fluid chromatography 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.

Original languageEnglish
JournalJournal of separation science
DOIs
Publication statusPublished - Jan 1 2019

Fingerprint

Tetrahydroisoquinolines
Carbolines
Stereoisomerism
Polysaccharides
Azepines
Chromatography
Fluids
Liquids
Isoquinolines
Enantiomers
Liquid chromatography
Chemical analysis
Temperature

Keywords

  • benzazepine analogs
  • beta-carboline
  • high-performance liquid chromatography
  • subcritical fluid chromatography
  • tetrahydroisoquinoline

ASJC Scopus subject areas

  • Analytical Chemistry
  • Filtration and Separation

Cite this

@article{12ccc34f748e40b8968c38c41a34901a,
title = "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",
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 methods on polysaccharide-based chiral stationary phases. Separation of the stereoisomers was optimized in both subcritical fluid chromatography and normal phase liquid chromatographic modes by investigating the effects of the composition of the bulk solvent, temperature, and the structures of the analytes and selectors. Both normal phase liquid chromatography and subcritical fluid chromatography 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.",
keywords = "benzazepine analogs, beta-carboline, high-performance liquid chromatography, subcritical fluid chromatography, tetrahydroisoquinoline",
author = "Attila Bajtai and Gyula Lajk{\'o} and G{\'a}bor N{\'e}meti and I. Szatm{\'a}ri and F. F{\"u}l{\"o}p and A. P{\'e}ter and I. Ilisz",
year = "2019",
month = "1",
day = "1",
doi = "10.1002/jssc.201900228",
language = "English",
journal = "Journal of Separation Science",
issn = "1615-9306",
publisher = "Wiley-VCH Verlag",

}

TY - JOUR

T1 - 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

AU - Bajtai, Attila

AU - Lajkó, Gyula

AU - Németi, Gábor

AU - Szatmári, I.

AU - Fülöp, F.

AU - Péter, A.

AU - Ilisz, I.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - 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 methods on polysaccharide-based chiral stationary phases. Separation of the stereoisomers was optimized in both subcritical fluid chromatography and normal phase liquid chromatographic modes by investigating the effects of the composition of the bulk solvent, temperature, and the structures of the analytes and selectors. Both normal phase liquid chromatography and subcritical fluid chromatography 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.

AB - 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 methods on polysaccharide-based chiral stationary phases. Separation of the stereoisomers was optimized in both subcritical fluid chromatography and normal phase liquid chromatographic modes by investigating the effects of the composition of the bulk solvent, temperature, and the structures of the analytes and selectors. Both normal phase liquid chromatography and subcritical fluid chromatography 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.

KW - benzazepine analogs

KW - beta-carboline

KW - high-performance liquid chromatography

KW - subcritical fluid chromatography

KW - tetrahydroisoquinoline

UR - http://www.scopus.com/inward/record.url?scp=85068533002&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85068533002&partnerID=8YFLogxK

U2 - 10.1002/jssc.201900228

DO - 10.1002/jssc.201900228

M3 - Article

C2 - 31216124

AN - SCOPUS:85068533002

JO - Journal of Separation Science

JF - Journal of Separation Science

SN - 1615-9306

ER -