Cargando…
Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides
Phenol amides are bioactive compounds naturally present in many plants. This class of compounds is known for antioxidant, anti-inflammatory, and anticancer activities. To better understand the reactivity and structure–bioactivity relationships of phenol amides, a large set of structurally diverse pu...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9000787/ https://www.ncbi.nlm.nih.gov/pubmed/35408599 http://dx.doi.org/10.3390/molecules27072203 |
_version_ | 1784685521322115072 |
---|---|
author | van Zadelhoff, Annemiek Vincken, Jean-Paul de Bruijn, Wouter J. C. |
author_facet | van Zadelhoff, Annemiek Vincken, Jean-Paul de Bruijn, Wouter J. C. |
author_sort | van Zadelhoff, Annemiek |
collection | PubMed |
description | Phenol amides are bioactive compounds naturally present in many plants. This class of compounds is known for antioxidant, anti-inflammatory, and anticancer activities. To better understand the reactivity and structure–bioactivity relationships of phenol amides, a large set of structurally diverse pure compounds are needed, however purification from plants is inefficient and laborious. Existing syntheses require multiple steps, including protection of functional groups and are generally overly complicated and only suitable for specific combinations of hydroxycinnamic acid and amine. Thus, to facilitate further studies on these promising compounds, we aimed to develop a facile general synthetic route to obtain phenol amides with a wide structural diversity. The result is a protocol for straightforward one-pot synthesis of phenol amides at room temperature within 25 h using equimolar amounts of N,N′-dicyclohexylcarbodiimide (DCC), amine, hydroxycinnamic acid, and sodium bicarbonate in aqueous acetone. Eight structurally diverse phenol amides were synthesized and fully chemically characterized. The facile synthetic route described in this work is suitable for a wide variety of biologically relevant phenol amides, consisting of different hydroxycinnamic acid subunits (coumaric acid, ferulic acid, and sinapic acid) and amine subunits (agmatine, anthranilic acid, putrescine, serotonin, tyramine, and tryptamine) with yields ranging between 14% and 24%. |
format | Online Article Text |
id | pubmed-9000787 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-90007872022-04-12 Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides van Zadelhoff, Annemiek Vincken, Jean-Paul de Bruijn, Wouter J. C. Molecules Communication Phenol amides are bioactive compounds naturally present in many plants. This class of compounds is known for antioxidant, anti-inflammatory, and anticancer activities. To better understand the reactivity and structure–bioactivity relationships of phenol amides, a large set of structurally diverse pure compounds are needed, however purification from plants is inefficient and laborious. Existing syntheses require multiple steps, including protection of functional groups and are generally overly complicated and only suitable for specific combinations of hydroxycinnamic acid and amine. Thus, to facilitate further studies on these promising compounds, we aimed to develop a facile general synthetic route to obtain phenol amides with a wide structural diversity. The result is a protocol for straightforward one-pot synthesis of phenol amides at room temperature within 25 h using equimolar amounts of N,N′-dicyclohexylcarbodiimide (DCC), amine, hydroxycinnamic acid, and sodium bicarbonate in aqueous acetone. Eight structurally diverse phenol amides were synthesized and fully chemically characterized. The facile synthetic route described in this work is suitable for a wide variety of biologically relevant phenol amides, consisting of different hydroxycinnamic acid subunits (coumaric acid, ferulic acid, and sinapic acid) and amine subunits (agmatine, anthranilic acid, putrescine, serotonin, tyramine, and tryptamine) with yields ranging between 14% and 24%. MDPI 2022-03-28 /pmc/articles/PMC9000787/ /pubmed/35408599 http://dx.doi.org/10.3390/molecules27072203 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 | Communication van Zadelhoff, Annemiek Vincken, Jean-Paul de Bruijn, Wouter J. C. Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides |
title | Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides |
title_full | Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides |
title_fullStr | Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides |
title_full_unstemmed | Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides |
title_short | Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides |
title_sort | facile amidation of non-protected hydroxycinnamic acids for the synthesis of natural phenol amides |
topic | Communication |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9000787/ https://www.ncbi.nlm.nih.gov/pubmed/35408599 http://dx.doi.org/10.3390/molecules27072203 |
work_keys_str_mv | AT vanzadelhoffannemiek facileamidationofnonprotectedhydroxycinnamicacidsforthesynthesisofnaturalphenolamides AT vinckenjeanpaul facileamidationofnonprotectedhydroxycinnamicacidsforthesynthesisofnaturalphenolamides AT debruijnwouterjc facileamidationofnonprotectedhydroxycinnamicacidsforthesynthesisofnaturalphenolamides |