Synthesis and Antimicrobial Activity of the Pathogenic <i>E. coli</i> Strains of <i>p</i>-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones
A mild and efficient protocol for the synthesis of <i>p</i>-quinols under aqueous conditions was developed. The pivotal role of additives in the copper-catalyzed addition of aryl boronic and heteroaryl boronic acids to benzoquinones was observed. It was found that polyvinylpyrrolidone (P...
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MDPI AG
2023-01-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/2/1623 |
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| author | Dominik Koszelewski Paweł Kowalczyk Jan Samsonowicz-Górski Anastasiia Hrunyk Anna Brodzka Justyna Łęcka Karol Kramkowski Ryszard Ostaszewski |
| author_facet | Dominik Koszelewski Paweł Kowalczyk Jan Samsonowicz-Górski Anastasiia Hrunyk Anna Brodzka Justyna Łęcka Karol Kramkowski Ryszard Ostaszewski |
| author_sort | Dominik Koszelewski |
| collection | DOAJ |
| description | A mild and efficient protocol for the synthesis of <i>p</i>-quinols under aqueous conditions was developed. The pivotal role of additives in the copper-catalyzed addition of aryl boronic and heteroaryl boronic acids to benzoquinones was observed. It was found that polyvinylpyrrolidone (PVP) was the most efficient additive used for the studied reaction. The noteworthy advantages of this procedure include its broad substrate scope, high yields up to 91%, atom economy, and usage of readily available starting materials. Another benefit of this method is the reusability of the catalytic system up to four times. Further, the obtained <i>p</i>-quinols were characterized on the basis of their antimicrobial activities against <i>E. coli</i>. Antimicrobial activity was further compared with the corresponding 4-benzoquinones and 4-hydroquinones. Among tested compounds, seven derivatives showed an antimicrobial activity profile similar to that observed for commonly used antibiotics such as ciprofloxacin, bleomycin, and cloxacillin. In addition, the obtained <i>p</i>-quinols constitute a suitable platform for further modifications, allowing for a convenient change in their biological activity profile. |
| first_indexed | 2024-03-09T12:19:24Z |
| format | Article |
| id | doaj.art-f85152444d484e529779ece69aed0e38 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T12:19:24Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-f85152444d484e529779ece69aed0e382023-11-30T22:43:12ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-01-01242162310.3390/ijms24021623Synthesis and Antimicrobial Activity of the Pathogenic <i>E. coli</i> Strains of <i>p</i>-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to BenzoquinonesDominik Koszelewski0Paweł Kowalczyk1Jan Samsonowicz-Górski2Anastasiia Hrunyk3Anna Brodzka4Justyna Łęcka5Karol Kramkowski6Ryszard Ostaszewski7Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandDepartment of Animal Nutrition, The Kielanowski Institute of Animal Physiology and Nutrition, Polish Academy of Sciences, Instytucka 3, 05-110 Jabłonna, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandDepartment of Physical Chemistry, Medical University of Bialystok, Kilińskiego 1 Str., 15-089 Białystok, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandA mild and efficient protocol for the synthesis of <i>p</i>-quinols under aqueous conditions was developed. The pivotal role of additives in the copper-catalyzed addition of aryl boronic and heteroaryl boronic acids to benzoquinones was observed. It was found that polyvinylpyrrolidone (PVP) was the most efficient additive used for the studied reaction. The noteworthy advantages of this procedure include its broad substrate scope, high yields up to 91%, atom economy, and usage of readily available starting materials. Another benefit of this method is the reusability of the catalytic system up to four times. Further, the obtained <i>p</i>-quinols were characterized on the basis of their antimicrobial activities against <i>E. coli</i>. Antimicrobial activity was further compared with the corresponding 4-benzoquinones and 4-hydroquinones. Among tested compounds, seven derivatives showed an antimicrobial activity profile similar to that observed for commonly used antibiotics such as ciprofloxacin, bleomycin, and cloxacillin. In addition, the obtained <i>p</i>-quinols constitute a suitable platform for further modifications, allowing for a convenient change in their biological activity profile.https://www.mdpi.com/1422-0067/24/2/1623<i>p</i>-quinolschemoselectivitycopper-catalyzed additionpolyvinylpyrrolidone (PVP)copper metal–organic frameworks (Cu-MOF)additives |
| spellingShingle | Dominik Koszelewski Paweł Kowalczyk Jan Samsonowicz-Górski Anastasiia Hrunyk Anna Brodzka Justyna Łęcka Karol Kramkowski Ryszard Ostaszewski Synthesis and Antimicrobial Activity of the Pathogenic <i>E. coli</i> Strains of <i>p</i>-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones International Journal of Molecular Sciences <i>p</i>-quinols chemoselectivity copper-catalyzed addition polyvinylpyrrolidone (PVP) copper metal–organic frameworks (Cu-MOF) additives |
| title | Synthesis and Antimicrobial Activity of the Pathogenic <i>E. coli</i> Strains of <i>p</i>-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones |
| title_full | Synthesis and Antimicrobial Activity of the Pathogenic <i>E. coli</i> Strains of <i>p</i>-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones |
| title_fullStr | Synthesis and Antimicrobial Activity of the Pathogenic <i>E. coli</i> Strains of <i>p</i>-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones |
| title_full_unstemmed | Synthesis and Antimicrobial Activity of the Pathogenic <i>E. coli</i> Strains of <i>p</i>-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones |
| title_short | Synthesis and Antimicrobial Activity of the Pathogenic <i>E. coli</i> Strains of <i>p</i>-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones |
| title_sort | synthesis and antimicrobial activity of the pathogenic i e coli i strains of i p i quinols additive effects of copper catalyzed addition of aryl boronic acid to benzoquinones |
| topic | <i>p</i>-quinols chemoselectivity copper-catalyzed addition polyvinylpyrrolidone (PVP) copper metal–organic frameworks (Cu-MOF) additives |
| url | https://www.mdpi.com/1422-0067/24/2/1623 |
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