Studies on Angiotensin Converting Enzyme Inhibitors. III. 2-Carboxyethylcarbamoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid Derivatives
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概要
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(3S)-2-[N-Substituted N-(2-carboxyethyl) carbamoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivaties (8a-d and 12a-t) and their monoester compounds (13a-k) were synthesized by condensation of (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylates (6a, b), 3-aminopropionates (5a, b or 10a-m) and phosgene, followed by deprotection of ester groups. Their in vitro angiotensin converting enzyme (ACE) inhibitory activities and antihypertensive effects were evaluated, and the structure-activity relationship is discussed. Some of the N-ethylcarbamoyl analogs (12h, 12j, 12k, 12l and 12o), which had hydrophobic substituents (C_8H_<17>-C_<12>H_<25>, CH_2CH_2Ph) at the α-position to the carboxyl group in the side chain, showed potent in vitro ACE inhibitory activities with IC_<50> values of 4.0-8.8×10^-9M. The monoesters 13e, 13h, and 13i reduced the systolic blood pressure by more than 30 mmHg in spontaneously hypertensive rats (SHR) at an oral dose of 50mg/kg.
- 1985-05-25
著者
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沼波 憲一
生化研
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米田 直人
Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
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沼波 憲一
Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
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米田 直人
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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加藤 錠治
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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林 公明
Research Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.
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坂井 和夫
Research Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.
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尾崎 泰彦
Research Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.
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木梨 計三
Safety Research Laboratory Tanabe Seiyaku Co., Ltd.
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坂井 和夫
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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尾崎 泰彦
Research Laboratory Of Applied Biochemistry Tanabe Seiyaku Co. Ltd.
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林 公明
Research Laboratory Of Applied Biochemistry:tanabe Seiyaku Co. Ltd.
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木梨 計三
Safety Research Laboratory Tanabe Seiyaku Co. Ltd.
-
米田 直人
Research Laboratory of Applied Biochemistry
-
米田 直人
Research Laboratory of Applied Biochemistry Tanabe Seiyaku Co., Ltd.
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尾崎 泰彦
Research Laboratory of Applied Biochemistry
-
林 公明
Research Laboratory of Applied Biochemistry
-
沼波 憲一
Research Laboratory of Applied Biochemistry
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