Synthesis of Novel Conjugates of Tetraoxane Endoperoxide with Bis(Quaternary Ammonium Salts)

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  • KUMURA Naokazu
    Division of Bioscience, Graduate School of Natural Science and Technology, Okayama University
  • FURUKAWA Hirotaka
    Division of Bioscience, Graduate School of Natural Science and Technology, Okayama University
  • KOBAYASHI Michiyo
    Division of Bioscience, Graduate School of Natural Science and Technology, Okayama University
  • ONYANGO Arnold N.
    Department of Food Science and Postharvest Technology, Jomo Kenyatta University of Agriculture and Technology
  • IZUMI Minoru
    Division of Bioscience, Graduate School of Natural Science and Technology, Okayama University
  • NAKAJIMA Shuhei
    Division of Bioscience, Graduate School of Natural Science and Technology, Okayama University
  • KIM Hye-Sook
    Faculty of Pharmaceutical Science, Graduate School of Medicine, Dentistry and Pharmaceutical Science, Okayama University
  • WATAYA Yusuke
    Faculty of Pharmaceutical Science, Graduate School of Medicine, Dentistry and Pharmaceutical Science, Okayama University
  • BABA Naomichi
    Division of Bioscience, Graduate School of Natural Science and Technology, Okayama University

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Novel water-soluble conjugates of 1,2,4,5-tetraoxane bis(quaternary ammonium salts) were synthesized in a relatively stable crystalline form via four steps starting from methyltrioxorhenium-catalyzed endo-peroxidation of ethyl 4-oxocyclohexanecarboxylate with hydrogen peroxide in hexafluoro-2-propanol. The assay for the in vitro toxicity of water-soluble tetraoxanes 5a–5d to malaria parasites indicate that they were inactive against the Plasmodium falciparum FCR-3 strain.

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