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Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity
Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon–carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the s...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9325161/ https://www.ncbi.nlm.nih.gov/pubmed/35889484 http://dx.doi.org/10.3390/molecules27144612 |
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author | Kalyaev, Mikhail V. Ryabukhin, Dmitry S. Borisova, Marina A. Ivanov, Alexander Yu. Boyarskaya, Irina A. Borovkova, Kristina E. Nikiforova, Lia R. Salmova, Julia V. Ul’yanovskii, Nikolay V. Kosyakov, Dmitry S. Vasilyev, Aleksander V. |
author_facet | Kalyaev, Mikhail V. Ryabukhin, Dmitry S. Borisova, Marina A. Ivanov, Alexander Yu. Boyarskaya, Irina A. Borovkova, Kristina E. Nikiforova, Lia R. Salmova, Julia V. Ul’yanovskii, Nikolay V. Kosyakov, Dmitry S. Vasilyev, Aleksander V. |
author_sort | Kalyaev, Mikhail V. |
collection | PubMed |
description | Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon–carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the starting furan acids and esters should be reactive electrophilic species in these transformations. Starting compounds and their hydroarylation products, at a concentration of 64 µg/mL, demonstrate good antimicrobial activity against yeast-like fungi Candida albicans. Apart from that, these compounds suppress Escherichia coli and Staphylococcus aureus. |
format | Online Article Text |
id | pubmed-9325161 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-93251612022-07-27 Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity Kalyaev, Mikhail V. Ryabukhin, Dmitry S. Borisova, Marina A. Ivanov, Alexander Yu. Boyarskaya, Irina A. Borovkova, Kristina E. Nikiforova, Lia R. Salmova, Julia V. Ul’yanovskii, Nikolay V. Kosyakov, Dmitry S. Vasilyev, Aleksander V. Molecules Article Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon–carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the starting furan acids and esters should be reactive electrophilic species in these transformations. Starting compounds and their hydroarylation products, at a concentration of 64 µg/mL, demonstrate good antimicrobial activity against yeast-like fungi Candida albicans. Apart from that, these compounds suppress Escherichia coli and Staphylococcus aureus. MDPI 2022-07-19 /pmc/articles/PMC9325161/ /pubmed/35889484 http://dx.doi.org/10.3390/molecules27144612 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 Kalyaev, Mikhail V. Ryabukhin, Dmitry S. Borisova, Marina A. Ivanov, Alexander Yu. Boyarskaya, Irina A. Borovkova, Kristina E. Nikiforova, Lia R. Salmova, Julia V. Ul’yanovskii, Nikolay V. Kosyakov, Dmitry S. Vasilyev, Aleksander V. Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity |
title | Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity |
title_full | Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity |
title_fullStr | Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity |
title_full_unstemmed | Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity |
title_short | Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity |
title_sort | synthesis of 3-aryl-3-(furan-2-yl)propanoic acid derivatives, and study of their antimicrobial activity |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9325161/ https://www.ncbi.nlm.nih.gov/pubmed/35889484 http://dx.doi.org/10.3390/molecules27144612 |
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