Synthesis and Antioxidative Properties of 1,2,3,4-Tetrahydropyridine Derivatives with Different Substituents in 4-Position

Natural products are an excellent source of inspiration for the development of new drugs. Among them, betalains have been extensively studied for their antioxidant properties and potential application as natural food dyes. Herein, we describe the seven-step synthesis of new betalamic acid analogs wi...

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Autores principales: Aiello, Daniele, Jonas, Hendrik, Carbone, Anna, Carbone, Daniela, Pecoraro, Camilla, Tesoriere, Luisa, Köhler, Jens, Wünsch, Bernhard, Diana, Patrizia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9658173/
https://www.ncbi.nlm.nih.gov/pubmed/36364252
http://dx.doi.org/10.3390/molecules27217423
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author Aiello, Daniele
Jonas, Hendrik
Carbone, Anna
Carbone, Daniela
Pecoraro, Camilla
Tesoriere, Luisa
Köhler, Jens
Wünsch, Bernhard
Diana, Patrizia
author_facet Aiello, Daniele
Jonas, Hendrik
Carbone, Anna
Carbone, Daniela
Pecoraro, Camilla
Tesoriere, Luisa
Köhler, Jens
Wünsch, Bernhard
Diana, Patrizia
author_sort Aiello, Daniele
collection PubMed
description Natural products are an excellent source of inspiration for the development of new drugs. Among them, betalains have been extensively studied for their antioxidant properties and potential application as natural food dyes. Herein, we describe the seven-step synthesis of new betalamic acid analogs without carboxy groups in the 2- and 6-position with an overall yield of ~70%. The Folin–Ciocalteu assay was used to determine the antioxidant properties of protected intermediate 21. Additionally, the five-step synthesis of betalamic acid analog 35 with three ester moieties was performed. Using NMR techniques, the stability of the obtained compounds towards oxygen was analyzed.
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spelling pubmed-96581732022-11-15 Synthesis and Antioxidative Properties of 1,2,3,4-Tetrahydropyridine Derivatives with Different Substituents in 4-Position Aiello, Daniele Jonas, Hendrik Carbone, Anna Carbone, Daniela Pecoraro, Camilla Tesoriere, Luisa Köhler, Jens Wünsch, Bernhard Diana, Patrizia Molecules Article Natural products are an excellent source of inspiration for the development of new drugs. Among them, betalains have been extensively studied for their antioxidant properties and potential application as natural food dyes. Herein, we describe the seven-step synthesis of new betalamic acid analogs without carboxy groups in the 2- and 6-position with an overall yield of ~70%. The Folin–Ciocalteu assay was used to determine the antioxidant properties of protected intermediate 21. Additionally, the five-step synthesis of betalamic acid analog 35 with three ester moieties was performed. Using NMR techniques, the stability of the obtained compounds towards oxygen was analyzed. MDPI 2022-11-01 /pmc/articles/PMC9658173/ /pubmed/36364252 http://dx.doi.org/10.3390/molecules27217423 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Aiello, Daniele
Jonas, Hendrik
Carbone, Anna
Carbone, Daniela
Pecoraro, Camilla
Tesoriere, Luisa
Köhler, Jens
Wünsch, Bernhard
Diana, Patrizia
Synthesis and Antioxidative Properties of 1,2,3,4-Tetrahydropyridine Derivatives with Different Substituents in 4-Position
title Synthesis and Antioxidative Properties of 1,2,3,4-Tetrahydropyridine Derivatives with Different Substituents in 4-Position
title_full Synthesis and Antioxidative Properties of 1,2,3,4-Tetrahydropyridine Derivatives with Different Substituents in 4-Position
title_fullStr Synthesis and Antioxidative Properties of 1,2,3,4-Tetrahydropyridine Derivatives with Different Substituents in 4-Position
title_full_unstemmed Synthesis and Antioxidative Properties of 1,2,3,4-Tetrahydropyridine Derivatives with Different Substituents in 4-Position
title_short Synthesis and Antioxidative Properties of 1,2,3,4-Tetrahydropyridine Derivatives with Different Substituents in 4-Position
title_sort synthesis and antioxidative properties of 1,2,3,4-tetrahydropyridine derivatives with different substituents in 4-position
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9658173/
https://www.ncbi.nlm.nih.gov/pubmed/36364252
http://dx.doi.org/10.3390/molecules27217423
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