5-Phosponohydantoins: synthesis and investigation of their biological activities

5-Phosponohydantoins: synthesis and investigation of their biological activities | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article 5-Phosponohydantoins: synthesis and investigation of their biological activities Ivan A. Klimchuk, Dmitry O. Shkil, Yury V. Timchenko, Arsenii A. Timichev, and 11 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-6630429/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 08 Sep, 2025 Read the published version in Monatshefte für Chemie - Chemical Monthly → Version 1 posted 4 You are reading this latest preprint version Abstract Various 5-phosphono-hydantoins resembling SF2312 and bearing phosphonate moiety can be prepared from the starting hydantoins by a previously described two-step process via sequential bromination and phosphorylation to yield diethyl 5-phosphono-hydantoin esters followed by facile removal of ethyl groups. The insights of two-step bromination and phosphorylation were analyzed and described in respect of the known literature data. Given the structural similarity between hydantoin derivatives and glyphosate, we propose that hydantoins with a phosphonate group could serve as potential modulators of EPSP synthase mimicking glyphosate’s binding interactions and disrupting the shikimate pathway. During a test on hypersensitive E. coli strains, some hydantoins bearing phosphonate moiety showed a slight antibiotic activity and additionally were shown to have phytotoxicity causing local chlorotic lesions on punctured leaf segments of three plant species. Molecular modelling was applied to understand the biological activity of synthesized hydantoins. Hydantoins 5-Bromohydantoins 5-Phosphonohydantoins N-Acyliminium cation Antimicrobial activity Phytotoxicity Molecular modelling Full Text Supplementary Files 22.Supportinginformation.docx Cite Share Download PDF Status: Published Journal Publication published 08 Sep, 2025 Read the published version in Monatshefte für Chemie - Chemical Monthly → Version 1 posted Reviewers agreed at journal 22 Jun, 2025 Reviewers invited by journal 20 Jun, 2025 Editor assigned by journal 13 May, 2025 First submitted to journal 10 May, 2025 You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-6630429","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":474137010,"identity":"ceed3df7-94aa-4f72-90ce-da829ab5b16a","order_by":0,"name":"Ivan A. 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