Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents; III Optically Active Isomers of Ar-Methyl-2-(2-(2-(4-phenylpiperazino)-ethoxy)phenyl)thiazolidine-3-carboxamides(Medicinal Chemistry,Chemical)

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概要

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• Optically active isomers of N-methyl-2-(2-(2-(4-phenylpiperazino)ethoxy)phenyl)thiazolidine-3-carboxamides ((+)-2 and (-)-2) have been synthesized and tested for positive inotropic activity. The racemic thiocarboxarnide ((±)-3) was resolved into the enantiomers ((+)-3 and (-)-3) via the L- and D-N-(2-naphthylsulfonyl)prolyl derivatives ((+)-4 and (-)-4). Conversion of the thiocarboxamides ((4-)-3 and (-)-3) to the carboxarnides ((+)-2 and (-)-2) was smoothly effected by treatment with the glycidic ester (7). The absolute stereochemistry of (-)-3 was determined to be 25 by X-ray crystallographic analysis. Hence, the absolute configuration of the carboxamide ((-)-2) is 2S. On i.v. administration to anesthetized dogs, the enantiomers of 2 showed only a threefold difference in positive inotropic activity, with the levo isomer ((-)-2) being the more active. In the isolated cat heart muscle, the enantiomers were nearly equipotent to each other. Thus, no significant difference between the positive inotropic activities of the optical isomers of 2 was observed.

• 社団法人日本薬学会の論文
• 1987-06-25

著者

• 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.

• 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.

• 中井 英雄

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

• 青江 啓一

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

• 関根 康雄

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 小寺 啓司

  Organic Chemistry Research Laboratory and Analytical Center, Tanabe Seiyaku Co., Ltd.

• 和田 博

  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

• 小寺 啓司

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co Ltd.

• 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

• 武田 幹男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 小田 邦幸

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 青江 啓一

  Organic Chemistry Research Laboratory:tanabe Seiyaku Co. Ltd.

• 名手 博行

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

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