Relationship between the Metabolic Chiral Inversion and Chemical Structure of 4-Phenyl-4-oxobutanoic Acids, Derivatives of Anti-rheumatic Agent KE-298

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概要

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• The relationship between metabolic chiral inversion and chemical structure of various 4-phenyl-4-oxobutanoic acids (4-OBA), derivatives of anti-rheumatic agent KE-298 [2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid], was investigated in rats. Chiral inversion occurred with the thio-alkyl group, whereas the thio-acyl group played no role in the inversion of 4-OBA. A 2-methylene moiety was required for the inversion. When the 4-carbonyl moiety was removed, chiral inversion was significantly decreased, which provided an affinity for the intramitochondrial medium chain fatty acid CoA ligase. In addition, the distance between the chiral center and the carbonyl moiety was also an important factor for chiral inversion. While a sulfur atom was not indispensable for the chiral inversion, the existence of the sulfur atom influenced its affinity to the long chain fatty acid CoA ligase.

• 公益社団法人日本薬学会の論文
• 1997-01-15

著者

• Yoshida Hideo

  Department Of Pediatric Surgery Chiba University Graduate School Of Medicine

• HAYASHI Masahiro

  Faculty of Pharmaceutical Sciences, Science University of Tokyo

• SUWA Toshio

  Department of Drug Development Science & Clinical Evaluation, Kyoritsu University of Pharmacy

• KOHNO Yoshiro

  Department of Drug Metabolism, Medicinal Research Laboratory, Taisho Pharmaceutical Co., Ltd.

• Kohno Yoshiro

  大正製薬(株)開発研究所薬物動態研究室

• Kohno Yoshiro

  Department Of Drug Metabolism Medicinal Research Laboratory Taisho Pharmaceutical Co. Ltd.

• Suwa T

  大正製薬(株)開発研究所薬物動態研究室

• Suwa Toshio

  Dept.of Biochemistry Tokyo College Of Pharmacy:(present Address) Research Center Taisho Pharmaceutic

• Yoshida H

  Lab. Of Food & Nutritional Sciences Dep. Of Nutritional Sci. Kobe-gakuin Univ.

• Fukumoto Kyoko

  Department Of Pharmacokinetics Kyoto Pharmaceutical University

• FUKUSHIMA Kiyomi

  Department of Drug Metabolism, Taisho Pharmaceutical Research Center

• ENDO Hiromi

  Department of Drug Metabolism, Research Center, Taisho Pharmaceutical Co., Ltd.,

• Endo H

  Department Of Drug Metabolism Research Center Taisho Pharmacetutical Co. Ltd.

• Hayashi Masahiro

  Faculty Of Agriculture Miyazaki University

• Fukushima K

  大正製薬(株)開発研究所薬物動態研究室

• Yoshida Hideo

  Department Of Aeronautics And Astronautics Kyoto University

• Endo Hiromi

  Department of Chemical Engineering, Faculty of Engineering, Hiroshima University

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