Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. II. 2-(Phenylpiperazinoalkoxyphenyl)thiazolidine-3-thioearboxamides and the Corresponding Carboxamides(Medicinal Chemistry,Chemical)

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概要

• 論文の詳細を見る

• A large number of 2-(phenylpiperazinoalkoxyphenyl)thiazolidine-3-thiocarboxamides and the corresponding carboxamides (II) were synthesized and tested for inotropic activity in anesthetized dogs. Compounds II were prepared from a hydroxybenzaldehyde (III) through the intermediates (IV, V, and X). Structure-activity relationships (SAR) were investigated by varying the structural parameters. Transposition of the piperazinoalkoxyl group to the meta or para position from the ortho position caused a marked fall in activity. Conversion of the thiocarboxamido to a carboxamido group caused a marked increase in activity. This tendency was generally observed in this series of compounds and constitutes a major deviation from the SAR in the simple 2-phenylthiazolidine series. With regard to effects of the length of the aminoalkoxy chain, the ethoxy derivatives were generally more potent than higher analogues. Lengthening of the N-alkyl group in the (thio)carboxamido group generally caused a decrease in activity. Among the various derivatives synthesized, II_<15> was found to be approximately one hundred times more potent than amrinone with a long duration of action.

• 社団法人日本薬学会の論文
• 1987-06-25

著者

• 石田 昭彦

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 松木 健司

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 武田 幹男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 名手 博行

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 関根 康雄

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 小田 邦幸

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 本間 靖

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 和田 博

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 矢花 秀雄

  Biological Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 長尾 拓

  Biological Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 綱島 朗

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 大塚 久雄

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 中井 英雄

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 日野 裕

  Biological Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 日野 裕

  Biological Research Laboratory Tanabe Seiyaku Co. Ltd.

• 関根 康雄

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 大塚 久男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 和田 博

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co . Ltd.

• 綱島 朗

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 仲井 英雄

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 関根 康雄

  タナベセイヤク

• 長尾 拓

  Department Of Toxicology And Pharmacology Faculty Of Pharmaceutical Sciences University Of Tokyo

• 仲井 英夫

  田辺製薬研

• 中井 英雄

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 名手 博行

  タナベセイヤク

• Nakai H

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• Nate H

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 矢花 秀雄

  Department Of Toxicology And Pharmacology Faculty Of Pharmaceutical Sciences University Of Tokyo

• 大塚 久雄

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 本間 靖

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 武田 幹男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 小田 邦幸

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 松木 健司

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 名手 博行

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

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