Synthesis of novel <i>N</i>-(p-toluenesulfonyl)aminophosphonates and evaluation of their biological properties

Abstract

<p></p> <p>The synthesis of a series of <i>N</i>-sulfonylaminophosphonates <b>2aA-2dC</b> and evaluation of their cytotoxicity and ecotoxicity is described.</p> <p><i>N</i>-sulfonylaminophsophonates <b>2aA-2dC</b> were obtained by addition of dialkyl phosphites to azomethine bonds of sulfonimines <b>1a-d</b> in dichloromethane, and the reaction was mediated by potassium carbonate. Sulfonimines <b>1a-d</b> were synthesized by direct condensation of selected aldehydes with <i>p-</i>toluenesulfonamide catalyzed by titanium(IV) ethoxide.</p> <p>The cytotoxicity of compounds <b>2aB-2cB, 2aC-2cC, 2bA</b> and <b>2dA</b> against normal primary human lymphocytes, non-small cell lung cancer cells A549, promyelocytic leukemia cells HL-60 and glioblastoma astrocytoma cells U87 was found to be very low.</p> <p>The phytotoxicity of <b>2dC</b> against monocotyledonous oat (<i>A. sativa</i>) and dicotyledonous radish (<i>R. sativus</i>) was measured and the compound was found to be practically not toxic for two model plants. Lack of toxicity for marine bacteria <i>A. fischeri</i> has been also detected. However, the compound <b>2dC</b> was found to be significantly toxic for freshwater, European crustaceans <i>H. incongruens</i> (ostracods).</p

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