Synthesis and Antihypertensive Activity of 5-(2-Hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic Acids
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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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- 渡辺 敏郎
- Research Laboratory, Santen Pharmaceutical Co., Ltd.
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- 大矢 正雪
- Research Laboratory, Santen Pharmaceutical Co., Ltd.
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- 磯 正
- Research Laboratory, Santen Pharmaceutical Co., Ltd.
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- 岩尾 順一
- Research Laboratory, Santen Pharmaceutical Co., Ltd.
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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.
収録刊行物
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- Chemical & pharmaceutical bulletin
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Chemical & pharmaceutical bulletin 33 (11), 4836-4846, 1985-11-25
公益社団法人日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1571135652461235968
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- NII論文ID
- 110003625266
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- NII書誌ID
- AA00602100
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- ISSN
- 00092363
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- 本文言語コード
- en
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- データソース種別
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- CiNii Articles