Synthesis and Antimicrobial Activity of the Pathogenic E. coli Strains of p-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones

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dc.contributor.authorKoszelewski, Dominik
dc.contributor.authorKowalczyk, Paweł
dc.contributor.authorSamsonowicz-Górski, Jan
dc.contributor.authorHrunyk, Anastasiia
dc.contributor.authorBrodzka, Anna
dc.contributor.authorŁęcka, Justyna
dc.contributor.authorKramkowski, Karol
dc.contributor.authorOstaszewski, Ryszard
dc.contributor.editorHadjikakou, Sotiris K.
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciencesen
dc.contributor.organizationDepartment of Animal Nutrition, The Kielanowski Institute of Animal Physiology and Nutrition, Polish Academy of Sciencesen
dc.contributor.organizationDepartment of Physical Chemistry, Medical University of Bialystoken
dc.date.accessioned2023-01-23T18:15:49Z
dc.date.available2023-01-23T18:15:49Z
dc.date.issued2023
dc.description.abstractA mild and efficient protocol for the synthesis of p-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 p-quinols were characterized on the basis of their antimicrobial activities against E. coli. 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 p-quinols constitute a suitable platform for further modifications, allowing for a convenient change in their biological activity profile.en
dc.description.sponsorshipMedical University of Białystok Grant National Science Center Opus 22 Nr 2021/43/B/NZ7/01903 National Science Center, Poland project OPUS No. 2019/33/B/ST4/01118 COST Action CA18224 “Green Chemical Engineering Network towards upscaling sustainable processes”.
dc.identifier.citationKoszelewski, D.; Kowalczyk, P.; Samsonowicz-Górski, J.; Hrunyk, A.; Brodzka, A.; Łęcka, J.; Kramkowski, K.; Ostaszewski, R. Synthesis and Antimicrobial Activity of the Pathogenic E. coli Strains of p-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinones. Int. J. Mol. Sci. 2023, 24, 1623. https://doi.org/10.3390/ijms24021623en
dc.identifier.doi10.3390/ijms24021623
dc.identifier.issn1661-6596
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/22220
dc.language.isoen
dc.publisherMDPIen
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectp-quinolsen
dc.subjectchemoselectivityen
dc.subjectcopper-catalyzed additionen
dc.subjectpolyvinylpyrrolidone (PVP)en
dc.subjectcopper metal–organic frameworks (Cu-MOF)en
dc.subjectadditivesen
dc.subjectantimicrobial activityen
dc.subjectE. coli cellsen
dc.subjectMICen
dc.titleSynthesis and Antimicrobial Activity of the Pathogenic E. coli Strains of p-Quinols: Additive Effects of Copper-Catalyzed Addition of Aryl Boronic Acid to Benzoquinonesen
dc.typearticleen
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