Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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
_version_ 1784756980784562176
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
work_keys_str_mv AT kalyaevmikhailv synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity
AT ryabukhindmitrys synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity
AT borisovamarinaa synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity
AT ivanovalexanderyu synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity
AT boyarskayairinaa synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity
AT borovkovakristinae synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity
AT nikiforovaliar synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity
AT salmovajuliav synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity
AT ulyanovskiinikolayv synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity
AT kosyakovdmitrys synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity
AT vasilyevaleksanderv synthesisof3aryl3furan2ylpropanoicacidderivativesandstudyoftheirantimicrobialactivity