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Enantiomeric Separation of New Chiral Azole Compounds

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 i...

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Autores principales: Kenari, Marziyeh E., Putman, Joshua I., Singh, Ravi P., Fulton, Brandon B., Phan, Huy, Haimour, Reem K., Tse, Key, Berthod, Alain, Lovely, Carl J., Armstrong, Daniel W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7796373/
https://www.ncbi.nlm.nih.gov/pubmed/33406592
http://dx.doi.org/10.3390/molecules26010213
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author Kenari, Marziyeh E.
Putman, Joshua I.
Singh, Ravi P.
Fulton, Brandon B.
Phan, Huy
Haimour, Reem K.
Tse, Key
Berthod, Alain
Lovely, Carl J.
Armstrong, Daniel W.
author_facet Kenari, Marziyeh E.
Putman, Joshua I.
Singh, Ravi P.
Fulton, Brandon B.
Phan, Huy
Haimour, Reem K.
Tse, Key
Berthod, Alain
Lovely, Carl J.
Armstrong, Daniel W.
author_sort Kenari, Marziyeh E.
collection PubMed
description 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.
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spelling pubmed-77963732021-01-10 Enantiomeric Separation of New Chiral Azole Compounds Kenari, Marziyeh E. Putman, Joshua I. Singh, Ravi P. Fulton, Brandon B. Phan, Huy Haimour, Reem K. Tse, Key Berthod, Alain Lovely, Carl J. Armstrong, Daniel W. Molecules Article 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. MDPI 2021-01-04 /pmc/articles/PMC7796373/ /pubmed/33406592 http://dx.doi.org/10.3390/molecules26010213 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kenari, Marziyeh E.
Putman, Joshua I.
Singh, Ravi P.
Fulton, Brandon B.
Phan, Huy
Haimour, Reem K.
Tse, Key
Berthod, Alain
Lovely, Carl J.
Armstrong, Daniel W.
Enantiomeric Separation of New Chiral Azole Compounds
title Enantiomeric Separation of New Chiral Azole Compounds
title_full Enantiomeric Separation of New Chiral Azole Compounds
title_fullStr Enantiomeric Separation of New Chiral Azole Compounds
title_full_unstemmed Enantiomeric Separation of New Chiral Azole Compounds
title_short Enantiomeric Separation of New Chiral Azole Compounds
title_sort enantiomeric separation of new chiral azole compounds
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7796373/
https://www.ncbi.nlm.nih.gov/pubmed/33406592
http://dx.doi.org/10.3390/molecules26010213
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