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<p>A series of substituted <i>N</i>-phenoxyacetyltaurates was synthesized from the corresponding phenoxyacetates by the reaction with potassium taurate. The unusual solid-state structure was established for potassium salt of <i>N</i>-(4-chlorophenoxyacetyl)taurine. According to the X-ray diffraction data, it consists of three symmetry-independent layers. Apart from ionic interactions and hydrogen bonds, the layers are stabilized by weak C—H⋯Cl van der Waals interactions. <i>N</i>-Substituted potassium taurates effectively reduced the level of lipopolysaccharide-induced proinflammatory cytokines in Raw264,7 cells. <i>N</i>-(3-Methoxyphenoxyacetyl)taurine inhibited a broad spectrum of key inflammatory mediators. The evaluation of biosafety demonstrated the absence of cytotoxicity of the compounds under study.</p>

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Substituted N-phenoxyacetyltaurates: synthesis, structural features, and biological activity

  • 期刊论文

  • 发表日期：

    2025年9月1日

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  • D. I. Gonchar,
  • E. P. Kramarova,
  • T. A. Shmigol,
  • D. V. Tarasenko,
  • A. A. Korlykov,
  • A. A. Lagunin,
  • N. Yu. Karpechenko,
  • N. M. Kiseleva,
  • Yu. I. Baukov,
  • Vad. V. Negrebetsky

摘要

A series of substituted N-phenoxyacetyltaurates was synthesized from the corresponding phenoxyacetates by the reaction with potassium taurate. The unusual solid-state structure was established for potassium salt of N-(4-chlorophenoxyacetyl)taurine. According to the X-ray diffraction data, it consists of three symmetry-independent layers. Apart from ionic interactions and hydrogen bonds, the layers are stabilized by weak C—H⋯Cl van der Waals interactions. N-Substituted potassium taurates effectively reduced the level of lipopolysaccharide-induced proinflammatory cytokines in Raw264,7 cells. N-(3-Methoxyphenoxyacetyl)taurine inhibited a broad spectrum of key inflammatory mediators. The evaluation of biosafety demonstrated the absence of cytotoxicity of the compounds under study.