Supercritical fluid chromatographic chiral ...
Document type :
Article dans une revue scientifique: Article original
Title :
Supercritical fluid chromatographic chiral separation of potential P2RX7 antagonists containing one, two and three chiral centers
Author(s) :
Knavs, Naomi [Auteur]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Zubaş, Andreea [Auteur]
Alexandru Ioan Cuza University of Iași = Universitatea Alexandru Ioan Cuza din Iași [UAIC]
JUNIA [JUNIA]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Apostol, Georgiana [Auteur]
Alexandru Ioan Cuza University of Iași = Universitatea Alexandru Ioan Cuza din Iași [UAIC]
JUNIA [JUNIA]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Furman, Christophe [Auteur]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Nica, Adrian [Auteur]
Alexandru Ioan Cuza University of Iași = Universitatea Alexandru Ioan Cuza din Iași [UAIC]
JUNIA [JUNIA]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Chankvetadze, Bezhan [Auteur]
Tbilisi State University
Ghinet, Alina [Auteur]
Alexandru Ioan Cuza University of Iași = Universitatea Alexandru Ioan Cuza din Iași [UAIC]
JUNIA [JUNIA]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Lipka, Emmanuelle [Auteur correspondant]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Zubaş, Andreea [Auteur]
Alexandru Ioan Cuza University of Iași = Universitatea Alexandru Ioan Cuza din Iași [UAIC]
JUNIA [JUNIA]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Apostol, Georgiana [Auteur]
Alexandru Ioan Cuza University of Iași = Universitatea Alexandru Ioan Cuza din Iași [UAIC]
JUNIA [JUNIA]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Furman, Christophe [Auteur]

Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Nica, Adrian [Auteur]
Alexandru Ioan Cuza University of Iași = Universitatea Alexandru Ioan Cuza din Iași [UAIC]
JUNIA [JUNIA]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Chankvetadze, Bezhan [Auteur]
Tbilisi State University
Ghinet, Alina [Auteur]
Alexandru Ioan Cuza University of Iași = Universitatea Alexandru Ioan Cuza din Iași [UAIC]
JUNIA [JUNIA]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Lipka, Emmanuelle [Auteur correspondant]

Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Journal title :
Journal of Chromatography Open
Pages :
100129
Publisher :
Elsevier
Publication date :
2024-05
ISSN :
2772-3917
English keyword(s) :
Anti-inflammatory compounds
Polysaccharides-based stationary phases
Separation of stereoisomers
Supercritical fluid chromatography
Chiral compounds with multiple chiral centers
Small-scale preparative separation
Polysaccharides-based stationary phases
Separation of stereoisomers
Supercritical fluid chromatography
Chiral compounds with multiple chiral centers
Small-scale preparative separation
HAL domain(s) :
Chimie
English abstract : [en]
<div>Chiral compounds with multiple chiral centers Small-scale preparative separation A B S T R A C T<p>Eleven polysaccharide-based chiral stationary phases were screened to separate stereoisomers of six lactam derivatives ...
Show more ><div>Chiral compounds with multiple chiral centers Small-scale preparative separation A B S T R A C T<p>Eleven polysaccharide-based chiral stationary phases were screened to separate stereoisomers of six lactam derivatives by supercritical fluid chromatography (SFC). Those molecules are antagonists of the P2×7 receptor with potential anti-inflammatory activity. They present a mixture of either two enantiomers, or four or eight stereoisomers depending on the number of chiral centers in their structure. The effect of chiral stationary phase, either amylose-or cellulose-based, coated or immobilized, chlorinated or non-chlorinated, on retention and selectivity of those compounds was studied. The effect of the co-solvent nature (methanol, ethanol, propan-2-ol and acetonitrile) and percentage (15 to 40 %), temperature (20 to 45 • C) and backpressure (8 to 20 MPa) on the enantioseparation and retention of 1-(2-chlorobenzyl)-5-((4-methoxyphenyl)amino)pyrrolidin-2-one (compound 4) was thoroughly studied. Thus, optimal conditions were defined for each derivative in order to implement the preparative separation of the whole series, except of 1-((3,4-dimethoxyphenyl)(phenyl)methyl)-5-oxo-N-(1phenylethyl)pyrrolidine-2-carboxamide) (compound 6) for which none of the eleven columns could resolve the eight stereoisomers. The small-scale preparative separation of the enantiomers of the most promising derivative, i.e. 3-acetyl-1-(4-chlorophenyl)-N-(2,4-dichlorobenzyl)-5-oxopyrrolidine-2-carboxamide (compound 2), is presented.</p></div>Show less >
Show more ><div>Chiral compounds with multiple chiral centers Small-scale preparative separation A B S T R A C T<p>Eleven polysaccharide-based chiral stationary phases were screened to separate stereoisomers of six lactam derivatives by supercritical fluid chromatography (SFC). Those molecules are antagonists of the P2×7 receptor with potential anti-inflammatory activity. They present a mixture of either two enantiomers, or four or eight stereoisomers depending on the number of chiral centers in their structure. The effect of chiral stationary phase, either amylose-or cellulose-based, coated or immobilized, chlorinated or non-chlorinated, on retention and selectivity of those compounds was studied. The effect of the co-solvent nature (methanol, ethanol, propan-2-ol and acetonitrile) and percentage (15 to 40 %), temperature (20 to 45 • C) and backpressure (8 to 20 MPa) on the enantioseparation and retention of 1-(2-chlorobenzyl)-5-((4-methoxyphenyl)amino)pyrrolidin-2-one (compound 4) was thoroughly studied. Thus, optimal conditions were defined for each derivative in order to implement the preparative separation of the whole series, except of 1-((3,4-dimethoxyphenyl)(phenyl)methyl)-5-oxo-N-(1phenylethyl)pyrrolidine-2-carboxamide) (compound 6) for which none of the eleven columns could resolve the eight stereoisomers. The small-scale preparative separation of the enantiomers of the most promising derivative, i.e. 3-acetyl-1-(4-chlorophenyl)-N-(2,4-dichlorobenzyl)-5-oxopyrrolidine-2-carboxamide (compound 2), is presented.</p></div>Show less >
Language :
Anglais
Peer reviewed article :
Oui
Audience :
Internationale
Popular science :
Non
Collections :
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