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Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor

Several families of naturally occurring C-alkylated dihydrochalcones display a broad range of biological activities, including antimicrobial and cytotoxic properties, depending on their alkylation sidechain. The catalytic Friedel–Crafts alkylation of the readily available aglycon moiety of neohesper...

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Autores principales: Ardaillou, Anne, Alsarraf, Jérôme, Legault, Jean, Simard, François, Pichette, André
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8224620/
https://www.ncbi.nlm.nih.gov/pubmed/34067407
http://dx.doi.org/10.3390/antibiotics10060620
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author Ardaillou, Anne
Alsarraf, Jérôme
Legault, Jean
Simard, François
Pichette, André
author_facet Ardaillou, Anne
Alsarraf, Jérôme
Legault, Jean
Simard, François
Pichette, André
author_sort Ardaillou, Anne
collection PubMed
description Several families of naturally occurring C-alkylated dihydrochalcones display a broad range of biological activities, including antimicrobial and cytotoxic properties, depending on their alkylation sidechain. The catalytic Friedel–Crafts alkylation of the readily available aglycon moiety of neohesperidin dihydrochalcone was performed using cinnamyl, benzyl, and isoprenyl alcohols. This procedure provided a straightforward access to a series of derivatives that were structurally related to natural balsacones, uvaretin, and erioschalcones, respectively. The antibacterial and cytotoxic potential of these novel analogs was evaluated in vitro and highlighted some relations between the structure and the pharmacological properties of alkylated dihydrochalcones.
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spelling pubmed-82246202021-06-25 Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor Ardaillou, Anne Alsarraf, Jérôme Legault, Jean Simard, François Pichette, André Antibiotics (Basel) Article Several families of naturally occurring C-alkylated dihydrochalcones display a broad range of biological activities, including antimicrobial and cytotoxic properties, depending on their alkylation sidechain. The catalytic Friedel–Crafts alkylation of the readily available aglycon moiety of neohesperidin dihydrochalcone was performed using cinnamyl, benzyl, and isoprenyl alcohols. This procedure provided a straightforward access to a series of derivatives that were structurally related to natural balsacones, uvaretin, and erioschalcones, respectively. The antibacterial and cytotoxic potential of these novel analogs was evaluated in vitro and highlighted some relations between the structure and the pharmacological properties of alkylated dihydrochalcones. MDPI 2021-05-22 /pmc/articles/PMC8224620/ /pubmed/34067407 http://dx.doi.org/10.3390/antibiotics10060620 Text en © 2021 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
Ardaillou, Anne
Alsarraf, Jérôme
Legault, Jean
Simard, François
Pichette, André
Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor
title Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor
title_full Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor
title_fullStr Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor
title_full_unstemmed Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor
title_short Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor
title_sort hemisynthesis and biological evaluation of cinnamylated, benzylated, and prenylated dihydrochalcones from a common bio-sourced precursor
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8224620/
https://www.ncbi.nlm.nih.gov/pubmed/34067407
http://dx.doi.org/10.3390/antibiotics10060620
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