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

Abstract

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.