Journal article

Novel synthetic route for antimalarial benzo[a]phenoxazine derivative SSJ-183 and two active metabolites.

  • Mizukawa Y Drug Discovery Science Research Center, Hoshi University, 2-4-41 Ebara, Shinagawa, Tokyo 142-8501, Japan; Synstar Japan Co., Ltd, Orbic Bldg 3F, 2-9-46 Sakaecho, Odawara 250-0011, Japan.
  • Ge JF Drug Discovery Science Research Center, Hoshi University, 2-4-41 Ebara, Shinagawa, Tokyo 142-8501, Japan; College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215006, China.
  • Bakar Md A Drug Discovery Science Research Center, Hoshi University, 2-4-41 Ebara, Shinagawa, Tokyo 142-8501, Japan; Center for Advanced Research in Sciences, University of Dhaka, Bangladesh.
  • Itoh I Drug Discovery Science Research Center, Hoshi University, 2-4-41 Ebara, Shinagawa, Tokyo 142-8501, Japan; Synstar Japan Co., Ltd, Orbic Bldg 3F, 2-9-46 Sakaecho, Odawara 250-0011, Japan.
  • Scheurer C Swiss Tropical and Public Health Institute, Socinstrasse 57, 4002 Basel, Switzerland; University of Basel, CH-4003 Basel, Switzerland.
  • Wittlin S Swiss Tropical and Public Health Institute, Socinstrasse 57, 4002 Basel, Switzerland; University of Basel, CH-4003 Basel, Switzerland.
  • Brun R Swiss Tropical and Public Health Institute, Socinstrasse 57, 4002 Basel, Switzerland; University of Basel, CH-4003 Basel, Switzerland.
  • Matsuoka H School of Medicine, Department of Infection and Immunity, Division of Medical Zoology, Jichi Medical University, 3311-1 Yakushiji, Shimotsuke-shi 329-0498, Japan.
  • Ihara M Drug Discovery Science Research Center, Hoshi University, 2-4-41 Ebara, Shinagawa, Tokyo 142-8501, Japan. Electronic address: m-ihara@hoshi.ac.jp.
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  • 2014-05-27
Published in:
  • Bioorganic & medicinal chemistry. - 2014
English A productive synthesis of benzo[a]phenoxazine derivative SSJ-183 (1), a promising lead for antimalarial agents, was developed using a one pot procedure. Furthermore, N-deethylated metabolite 3 and bis-N,N-deethylated metabolite 4 were synthesized by the application of the method. The metabolites 3 and 4 showed comparable and ∼2-fold increased activities against drug-sensitive and drug-resistant Plasmodium falciparum parasites.
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  • English
Open access status
bronze
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https://folia.unifr.ch/global/documents/49535
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