Synthesis and Antihypertensive Activity of 5-(2-Hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic Acids
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概要
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The (2S, 5R)-(+)- or (2R, 5S)-(-)-thiol (4a or 4b) was synthesized by catalytic hydrogenation of the corresponding (S)-(-)- or (R)-(+)-pyrrolinecarboxylic acid (8a or 8b) resolved with (R)-(-)-1,2-diphenylethylamine, followed by acylation with 3-(benzoylthio) propionyl chloride and ammonolysis. The thiols were converted into the corresponding O, S-diacetates (16a and 16b), which were transformed into (2R, 5R)-(+)- and (2S, 5S)-(-)-thiols (18a and 18b) via their O, S-diacetates (17a and 17b) by epimerization and then ammonolysis. The stereochemistry of these thiols was elucidated on the basis of synthesis from tert-butoxycarbonyl-L-glutamic acid γ-benzylester (9) and proton nuclear magnetic resonance (^1H-NMR) analysis. The thiols were tested for inhibitory activity against angiotensin-converting enzyme in vitro. (2S, 5R)-5-(2-Hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acid (4a) showed the most potent activity among them.
- 社団法人日本薬学会の論文
- 1985-11-25
著者
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大矢 正雪
Research Laboratory Santen Pharmaceutical Co. Ltd.
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岩尾 順一
Research Laboratory, Santen Pharmaceutical Co., Ltd.
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河嶋 洋一
Central Research Laboratories, Santen Pharmaceutical Co., Ltd.,
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岩尾 順一
Central Research Laboratories Santen Pharmaceutical Co. Ltd.
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渡辺 敏郎
Research Laboratory, Santen Pharmaceutical Co., Ltd.
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渡辺 敏郎
Research Laboratory Santen Pharmaceutical Co. Ltd.
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河嶋 洋一
Central Research Laboratories Santen Pharmaceutical Co. Ltd.
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加藤 榮信
Research Laboratory, Santen Pharmaceutical Co., Ltd.
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山本 晃嗣
Research Laboratory, Santen Pharmaceutical Co., Ltd.
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河嶋 洋一
Research Laboratory, Santen Pharmaceutical Co., Ltd.
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磯 正
Research Laboratory, Santen Pharmaceutical Co., Ltd.
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山本 晃嗣
Central Research Laboratories Santen Pharmaceutical Co. Ltd.
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磯 正
Central Research Laboratories Santen Pharmaceutical Co. Ltd.
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加藤 榮信
Research Laboratory Santen Pharmaceutical Co. Ltd.
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加藤 栄信
参天製薬
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