Many commonly used drugs are chiral compounds. As known, drugs’ enantiomers are certainly characterized by identical physicochemical properties, but can differ in their pharmacokinetics, pharmacodynamics and toxicity. In connection with this, interest in chiral analysis and evaluation of stereolability of biologically active compounds has grown significantly in recent years. In this work, the stereochemical analysis of the chiral heterocyclic compound 1-[2-(2-methyl-2-methoxycarbonylacetamido) benzenesulfonyl]-1h-pyrrole [1] was carried out through the aid of two different analytical approaches: 1) kinetic batchwise studies monitored by enantioselective HPLC (eHPLC) technique; 2) kinetic on-column studies monitored by Dynamic enantioselective High Performance Liquid Chromatography (D-eHPLC). The chromatographic analyses were carried out by the commercially available Chiralcel OJ column. The study also covered the effects arising from the modification of the mobile phase, with variations concerning kind and polarity of the employed solvents, as well as the transition from normal to reverse phase, in presence or not of organic modifiers, such as triethylamine (TEA) and trifluoroacetic acid (TFA). All the resulting dynamic chromatograms were analysed by means of the home-made computer program Auto-DHPLC-y2k. Analysis of the obtained experimental data made it possible to achieve kinetic and thermodynamic information relevant to the enantiomerization/racemization process of the heterocyclic compound under consideration. [2,3] Finally, as the conclusive step of the investigation, the possible mechanisms responsible for the observed enantioisomerizations have been inquired by computational study.

Enantiomerization barrier of 1-[2-(2-methyl-2-methoxycarbonylacetamido) benzenesulfonyl]-1h-pyrrole studied by enantioselective dynamic HPLC, classical off column technique and computational approach / Buonsenso, Fabio; Cirilli, Roberto; Silvestri, Romano; Pierini, Marco. - (2021). ((Intervento presentato al convegno Merck Young Chemists' Symposium XX edition tenutosi a Rimini.

Enantiomerization barrier of 1-[2-(2-methyl-2-methoxycarbonylacetamido) benzenesulfonyl]-1h-pyrrole studied by enantioselective dynamic HPLC, classical off column technique and computational approach

Fabio Buonsenso
Primo
;
Romano Silvestri
Penultimo
;
Marco Pierini
Ultimo
2021

Abstract

Many commonly used drugs are chiral compounds. As known, drugs’ enantiomers are certainly characterized by identical physicochemical properties, but can differ in their pharmacokinetics, pharmacodynamics and toxicity. In connection with this, interest in chiral analysis and evaluation of stereolability of biologically active compounds has grown significantly in recent years. In this work, the stereochemical analysis of the chiral heterocyclic compound 1-[2-(2-methyl-2-methoxycarbonylacetamido) benzenesulfonyl]-1h-pyrrole [1] was carried out through the aid of two different analytical approaches: 1) kinetic batchwise studies monitored by enantioselective HPLC (eHPLC) technique; 2) kinetic on-column studies monitored by Dynamic enantioselective High Performance Liquid Chromatography (D-eHPLC). The chromatographic analyses were carried out by the commercially available Chiralcel OJ column. The study also covered the effects arising from the modification of the mobile phase, with variations concerning kind and polarity of the employed solvents, as well as the transition from normal to reverse phase, in presence or not of organic modifiers, such as triethylamine (TEA) and trifluoroacetic acid (TFA). All the resulting dynamic chromatograms were analysed by means of the home-made computer program Auto-DHPLC-y2k. Analysis of the obtained experimental data made it possible to achieve kinetic and thermodynamic information relevant to the enantiomerization/racemization process of the heterocyclic compound under consideration. [2,3] Finally, as the conclusive step of the investigation, the possible mechanisms responsible for the observed enantioisomerizations have been inquired by computational study.
978-88-94952-25-4
File allegati a questo prodotto
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1587169
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact