{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,10]],"date-time":"2026-02-10T01:46:44Z","timestamp":1770688004024,"version":"3.49.0"},"reference-count":31,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2022,10,13]],"date-time":"2022-10-13T00:00:00Z","timestamp":1665619200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Science Center","award":["2019\/33\/B\/ST4\/01118"],"award-info":[{"award-number":["2019\/33\/B\/ST4\/01118"]}]},{"name":"National Science Center","award":["SUB\/2\/DN\/22\/001\/2201"],"award-info":[{"award-number":["SUB\/2\/DN\/22\/001\/2201"]}]},{"name":"Medical University of Bia\u0142ystok","award":["2019\/33\/B\/ST4\/01118"],"award-info":[{"award-number":["2019\/33\/B\/ST4\/01118"]}]},{"name":"Medical University of Bia\u0142ystok","award":["SUB\/2\/DN\/22\/001\/2201"],"award-info":[{"award-number":["SUB\/2\/DN\/22\/001\/2201"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The impact of substituent at phenyl ring of diethyl benzylphosphonate derivatives on cytotoxic activity was studied. The organophosphonates were obtained based on developed palladium-catalyzed \u03b1, \u03b2-homodiarylation of vinyl esters protocol. The new synthetic pathway toward 1,2-bis(4-((diethoxyphosphoryl)methyl)phenyl)ethyl acetate was proposed which significantly improves the overall yield of the final product (from 1% to 38%). Several newly synthesized organophosphonates were tested as new potential antimicrobial drugs on model Escherichia coli bacterial strains (K12 and R2-R3). All tested compounds show the highest selectivity and activity against K12 and R2 strains. Preliminary cellular studies using MIC and MBC tests and digestion of Fpg after modification of bacterial DNA suggest that selected benzylphosphonate derivatives may have greater potential as antibacterial agents than typically used antibiotics such as ciprofloxacin, bleomycin and cloxacillin. These compounds are highly specific for pathogenic E. coli strains based on the model strains used and may be engaged in the future as new substitutes for commonly used antibiotics, which is especially important due to the increasing resistance of bacteria to various drugs and antibiotics.<\/jats:p>","DOI":"10.3390\/molecules27206865","type":"journal-article","created":{"date-parts":[[2022,10,13]],"date-time":"2022-10-13T22:21:11Z","timestamp":1665699671000},"page":"6865","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["The Synthesis and Evaluation of Diethyl Benzylphosphonates as Potential Antimicrobial Agents"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6659-0758","authenticated-orcid":false,"given":"Anna","family":"Brodzka","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry PAS, Kasprzaka 44\/52, 01-224 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4025-3750","authenticated-orcid":false,"given":"Pawe\u0142","family":"Kowalczyk","sequence":"additional","affiliation":[{"name":"Department of Animal Nutrition, The Kielanowski Institute of Animal Physiology and Nutrition, Polish Academy of Sciences, Instytucka 3, 05-110 Jab\u0142onna, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6435-624X","authenticated-orcid":false,"given":"Damian","family":"Trzepizur","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry PAS, Kasprzaka 44\/52, 01-224 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0968-3330","authenticated-orcid":false,"given":"Dominik","family":"Koszelewski","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry PAS, Kasprzaka 44\/52, 01-224 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Karol","family":"Kramkowski","sequence":"additional","affiliation":[{"name":"Department of Physical Chemistry, Medical University of Bialystok, Kili\u0144skiego 1 Str., 15-089 Bia\u0142ystok, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mateusz","family":"Szymczak","sequence":"additional","affiliation":[{"name":"Department of Molecular Virology, Institute of Microbiology, Faculty of Biology, University of Warsaw, Miecznikowa 1, 02-096 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0555-8690","authenticated-orcid":false,"given":"Aleksandra","family":"Wypych","sequence":"additional","affiliation":[{"name":"Centre for Modern Interdisciplinary Technologies, Nicolaus Copernicus University in Toru\u0144, Wile\u0144ska 4, 87-100 Toru\u0144, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6067-1469","authenticated-orcid":false,"given":"Rafa\u0142","family":"Lizut","sequence":"additional","affiliation":[{"name":"Institute of Mathematics, Informatics and Landscape Architecture, The John Paul II Catholic University of Lublin, 20-708 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3032-196X","authenticated-orcid":false,"given":"Ryszard","family":"Ostaszewski","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry PAS, Kasprzaka 44\/52, 01-224 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,10,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"5704","DOI":"10.1021\/acs.chemrev.6b00536","article-title":"Phosphonate Biochemistry","volume":"117","author":"Horsman","year":"2017","journal-title":"Chem. 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