Enantiomeric Separation of New Chiral Azole Compounds - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Molecules Année : 2021

Enantiomeric Separation of New Chiral Azole Compounds

Résumé

Twelve new azole compounds were synthesized through an ene reaction involving methylidene heterocycles and phenylmaleimide, producing four oxazoles, five thiazoles, and one pyridine derivative, and ethyl glyoxylate for an oxazole and a thiazole compound. The twelve azoles have a stereogenic center in their structure. Hence, a method to separate the enantiomeric pairs, must be provided if any further study of chemical and pharmacological importance of these compounds is to be accomplished. Six chiral stationary phases were assayed: four were based on macrocyclic glycopeptide selectors and two on linear carbohydrates, i.e., derivatized maltodextrin and amylose. The enantiomers of the entire set of new chiral azole compounds were separated using three different mobile phase elution modes: normal phase, polar organic, and reversed phase. The most effective chiral stationary phase was the MaltoShell column, which was able to separate ten of the twelve compounds in one elution mode or another. Structural similarities in the newly synthesized oxazoles provided some insights into possible chiral recognition mechanisms.
Fichier principal
Vignette du fichier
molecules-26-00213-v2.pdf (1.3 Mo) Télécharger le fichier
Origine : Fichiers éditeurs autorisés sur une archive ouverte

Dates et versions

hal-03318473 , version 1 (10-08-2021)

Identifiants

Citer

Marziyeh E Kenari, Joshua I Putman, Ravi P Singh, Brandon B Fulton, Huy Phan, et al.. Enantiomeric Separation of New Chiral Azole Compounds. Molecules, 2021, 26 (1), pp.213. ⟨10.3390/molecules26010213⟩. ⟨hal-03318473⟩
28 Consultations
49 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More