(2S,4S)-1-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-4-benzyl-pyrrolidine-2-carboxylic acid; compound with dicyclohexyl-amine | 82092-98-6

• 英文名称: (2S,4S)-1-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-4-benzyl-pyrrolidine-2-carboxylic acid; compound with dicyclohexyl-amine
• CAS: 82092-98-6
• 化学式: C₁₂H₂₃N*C₁₈H₂₃NO₄S
• 分子量: 530.772
• InChiKey: LMNDFJRIBFRZLQ-OCVYBSGDSA-N

反应信息

• 作为反应物：
  描述：

  (2S,4S)-1-((S)-3-Acetylsulfanyl-2-methyl-propionyl)-4-benzyl-pyrrolidine-2-carboxylic acid; compound with dicyclohexyl-amine 在 氨 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (2S,4S)-4-Benzyl-1-((S)-3-mercapto-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines

  摘要：

  Analogues of captopril, enalaprilat, and the phosphinic acid [hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline incorporating 4-substituted proline derivatives have been synthesized and evaluated as inhibitors of angiotensin-converting enzyme (ACE) in vitro and in vivo. The 4-substituted prolines, incorporating alkyl, aryl, alkoxy, aryloxy, alkylthio, and arylthio substituents were prepared from derivatives of 4-hydroxy- and 4-ketoproline. In general, analogues of all three classes of inhibitors with hydrophobic substituents on proline were more potent in vitro than the corresponding unsubstituted proline compounds. 4-Substituted analogues of captopril showed greater potency and duration of action than the parent compound as inhibitors of the angiotensin I induced pressor response in normotensive rats. The S-benzoyl derivative of cis-4-(phenylthio)captopril, zofenopril, was found to be one of the most potent compounds of this class and is now being evaluated clinically as an antihypertensive agent. In the phosphinic acid series, the 4-ethylenethioketal and trans-4-cyclohexyl derivatives were found to be the most potent compounds in vitro and in vivo. A prodrug of the latter compound, fosinopril, is also being evaluated in clinical trials.

  DOI：

  10.1021/jm00401a014