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

Naokazu KUMURA; Hirotaka FURUKAWA; Michiyo KOBAYASHI; Arnold N. ONYANGO; Minoru IZUMI; Shuhei NAKAJIMA; Hye-Sook KIM; Yusuke WATAYA; Naomichi BABA

doi:10.1271/bbb.80571

Organic Chemistry Notes

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

Naokazu KUMURA, Hirotaka FURUKAWA, Michiyo KOBAYASHI, Arnold N. ONYANGO, Minoru IZUMI, Shuhei NAKAJIMA, Hye-Sook KIM, Yusuke WATAYA, Naomichi BABA

Author information

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

Keywords: tetraoxane, bis(quaternary ammonium salts), malaria, reactive oxygen species

JOURNAL FREE ACCESS

2009 Volume 73 Issue 1 Pages 217-220

DOI https://doi.org/10.1271/bbb.80571

View "Advance Publication" version (January 7, 2009).

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Abstract

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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