Isoxazole Derivatives as Centrally Acting Muscle Relaxants. II. : Synthesis and Structure-Activity Relationship of 3-Amino-N-(3-phenyl-5-isoxazolyl)propanamides

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概要

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• N-Substituted 3-amino-2-methyl-N-(3-phenyl-5-isoxazolyl)propanamide derivatives (5a-w) were prepared, and their muscle relaxant and anticonvulsant activities were evaluatd. Among the compounds with high potency, 3-diethylamino-2,N-dimethyl-N-(3-phenyl-5-isoxazolyl)propanamide (5e) was found to possess selective muscle relaxant and anticonvulsant activities. Compounds with carbon side chains other than the 2-methylpropanamide moiety did not give increased muscle relaxant activity. Optical isomers of 5e were prepared from metyl (+)-and (-)-3-diethylamino-2-methylpropionates (15a, b), and the (+)-isomer (5x)b was found to be twice as potent as the (-)-isomer (5y). The structure-activity relationship was studied with emphasis on the effects of the 3-amino moiety and of the substituent on the isoxazolyl 5-amino group. A good quadratic correlation equation was found between hydrophobicity and muscle relaxant activity.

• 社団法人日本薬学会の論文
• 1986-04-25

著者

• 水柿 道直

  Pharmaceutical Institute Tohoku University

• 宮崎 浩

  日本化薬(株)経営企画室

• 坂本 尚夫

  Pharmaceutical Institute, Tohoku University

• 福田 英臣

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 福田 英臣

  Faculty Of Pharmaceutical Sciences The University Of Tokyo

• 舘江 栃郎

  Research Laboratories Of Pharmaceuticals Group Nippon Kayaku Co. Ltd.

• 蔵重 修二

  Research Laboratories of Pharmaceutical Division, Nippon Kayaku Co.

• 成田 和久

  Research Laboratories of Pharmaceuticals Group, Nippon Kayaku Co., Ltd.,

• 伊藤 真治

  Research Laboratories of Pharmaceuticals Group, Nippon Kayaku Co., Ltd.,

• 宮崎 浩

  Research Laboratories of Pharmaceuticals Group, Nippon Kayaku Co., Ltd.,

• YAMANAKA HIROSHI

  Pharmaceutical Institute, Tohoku University

• 成田 和久

  日本化薬

• 坂本 尚夫

  東北大院薬

• 坂本 尚夫

  Pharmaceutical Institute Tohoku University

• 坂本 尚夫

  東北大学大学院薬学研究科

• 伊藤 真治

  Research Laboratories Of Pharmaceuticals Group Nippon Kayaku Co. Ltd.

• Yamanaka Hiroshi

  Pharmaceutical Institute Tohoku University

• 蔵重 修二

  Research Laboratories of Pharmaceuticals Group, Nippon Kayaku CO., Ltd.,

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