ArticleMolecules (Basel, Switzerland)2021
Enantiomeric Separation of New Chiral Azole Compounds.
Article in Molecules (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Macrocyclic Glycopeptide-Based Chiral Stationary Phases Applied in Enantioselective Liquid Chromatographic Analyses: An Overview.Methods in molecular biology (Clifton, N.J.) · 2026Review
- Enantioseparation by zeolitic imidazolate framework-8-silica hybrid monolithic column with sulfobutylether-β-cyclodextrin as a chiral additive in capillary electrochromatography.Mikrochimica acta · 2023Article
- Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors.Molecules (Basel, Switzerland) · 2021Review
- An overview of chiral separations of pharmaceutically active substances by HPLC (2018-2020).Monatshefte fur chemie · 2021Review
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Authors and funding
10 authors.
Funding
Abstract
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 glyoxal 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 the 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.
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Registered trials
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