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<p>Various 5-phosphonohydantoins resembling 3-dihydroxyphosphoryl-1,5-dihydroxy-2-pyrrolidone (SF2312) and bearing a 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-phosphonohydantoin 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 <i>E. coli</i> strains, some hydantoins bearing phosphonate moiety showed 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.</p> Graphical abstract <p></p>

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5-Phosphonohydantoins: synthesis and investigation of their biological activities

  • 期刊论文

  • 发表日期：

    2025年9月8日

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  • Ivan A. Klimchuk,
  • Dmitry O. Shkil,
  • Yury V. Timchenko,
  • Arsenii A. Timichev,
  • Igor A. Rodin,
  • Vitaliy A. Ioutsi,
  • Garegin A. Petrosyan,
  • Dmitrii A. Lukianov,
  • Tingxuan Yan,
  • Jinlei Bian,
  • Natalya A. Pavlova,
  • Elizaveta G. Lukina,
  • Alexander O. Berestetskiy,
  • Elena K. Beloglazkina,
  • Alexander V. Finko

摘要

Various 5-phosphonohydantoins resembling 3-dihydroxyphosphoryl-1,5-dihydroxy-2-pyrrolidone (SF2312) and bearing a 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-phosphonohydantoin 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 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.

Graphical abstract