Studies on 2(1H)-Quinolinone Derivatives as Gastric Antiulcer Active Agents. Synthesis and Antiulcer Activities of Optically Active α-Amino Acid Derivatives of 2(1H)-Quinolinone and Oxindole(Medicinal Chemistry,Chemical)

  • 内多 稔
    Tokushima Research Institute, Otsuka Pharmaceutical Co., Ltd.
  • 田房 不二男
    Tokushima Research Institute, Otsuka Pharmaceutical Co., Ltd.
  • 小松 真
    Tokushima Research Institute, Otsuka Pharmaceutical Co., Ltd.
  • 森田 誠治
    Tokushima Research Institute, Otsuka Pharmaceutical Co., Ltd.
  • 神辺 敏実
    Tokushima Research Institute, Otsuka Pharmaceutical Co., Ltd.
  • 中川 量之
    Tokushima Research Institute, Otsuka Pharmaceutical Co., Ltd.

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In order to study the relationship of structure to antiulcer activity, optical active a-amino acid derivatives of 2(1H)-quinolinone and oxindole were synthesized and tested for antiulcer activity against acetic acid-induced gastric ulcer in rats. The enantiomers of 2(1H)-quinolinone derivatives were obtained by optical resolution with (-)-brucine. The oxindole derivatives having different absolute configurations at the a-amino acid moiety were synthesized by oxidation of N-(4-chlorobenzoyl)-L-or -D-tryptophan. The antiulcer activity did not seem to be influenced by the α-amino acid chirality.

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