Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reaction

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dc.contributor.authorKoszelewski, Dominik
dc.contributor.authorKowalczyk, Paweł
dc.contributor.authorŚmigielski, Paweł
dc.contributor.authorSamsonowicz-Górski, Jan
dc.contributor.authorKramkowski, Karol
dc.contributor.authorWypych, Aleksandra
dc.contributor.authorSzymczak, Mateusz
dc.contributor.authorOstaszewski, Ryszard
dc.contributor.editorStamboulis, Artemis
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.contributor.organizationCentre for Modern Interdisciplinary Technologies, Nicolaus Copernicus University, Toruńen
dc.contributor.organizationDepartment of Molecular Virology, Institute of Microbiology, Faculty of Biology, University of Warsawen
dc.date.accessioned2022-10-26T14:18:05Z
dc.date.available2022-10-26T14:18:05Z
dc.date.issued2022
dc.description.abstractWe reported a new method dealing with the synthesis of novel pharmacologically relevant α-aminophosphonate derivatives via a lipase-catalyzed Kabachnik−Fields reaction with yields of up to 93%. The advantages of this protocol are excellent yields, mild reaction conditions, low costs, and sustainability. The developed protocol is applicable to a range of H-phosphites and organic amines, providing a wide substrate scope. A new class of α-aminophosphonate analogues possessing P-chiral centers was also synthesized. The synthesized compounds were characterized on the basis of their antimicrobial activities against E. coli. The impact of the various alkoxy groups on antimicrobial activity was demonstrated. The crucial role of the substituents, located at the aromatic rings in the phenylethyloxy and benzyloxy groups, on the inhibitory action against selected pathogenic E. coli strains was revealed. The observed results are especially important because of increasing resistance of bacteria to various drugs and antibiotics.en
dc.description.sponsorshipMedical University of Białystok (grant SUB/2/DN/22/001/2201) National Science Center (OPUS No. 2019/33/B/ST4/01118)
dc.identifier.citationKoszelewski, D.; Kowalczyk, P.; ́Smigielski, P.; Samsonowicz-Górski, J.; Kramkowski, K.; Wypych, A.; Szymczak, M.; Ostaszewski, R. Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reaction. Materials 2022, 15, 3846. https:// doi.org/10.3390/ma15113846en
dc.identifier.doi10.3390/ma15113846
dc.identifier.issn1996-1944
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/21796
dc.language.isoen
dc.publisherMDPIen
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectα-aminophosphonatesen
dc.subjectKabachnik-Fields reactionen
dc.subjectantimicrobial activityen
dc.titleRelationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reactionen
dc.typearticleen
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