(S)-1-[(2S,3R)-3-Acetylsulfanyl-4-(4-bromo-phenyl)-2-methyl-4-oxo-butyryl]-pyrrolidine-2-carboxylic acid | 75382-15-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1-[(2S,3R)-3-Acetylsulfanyl-4-(4-bromo-phenyl)-2-methyl-4-oxo-butyryl]-pyrrolidine-2-carboxylic acid
• 英文别名: (2S)-1-[(2S,3R)-3-acetylsulfanyl-4-(4-bromophenyl)-2-methyl-4-oxobutanoyl]pyrrolidine-2-carboxylic acid
• CAS: 75382-15-9
• 化学式: C₁₈H₂₀BrNO₅S
• 分子量: 442.331
• InChiKey: UWIBVAUAEBBHOQ-FUEDEBDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-1-[(2S,3R)-3-Bromo-4-(4-bromo-phenyl)-2-methyl-4-oxo-butyryl]-pyrrolidine-2-carboxylic acid 、 potassium thioacetate 以 乙腈 为溶剂， 反应 18.0h， 以35%的产率得到(S)-1-[(2S,3R)-3-Acetylsulfanyl-4-(4-bromo-phenyl)-2-methyl-4-oxo-butyryl]-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Antihypertensive agents: angiotensin converting enzyme inhibitors. 1-[3-(Acylthio)-3-aroylpropionyl]-L-prolines

  摘要：

  A series of 1-[3-(acylthio)-3-aroylpropionyl]-L-proline derivatives was synthesized. A number of these compounds are potent angiotensin converting enzyme (ACE) inhibitors that lowered blood pressure in aorta-coarcted renal hypertensive rats. The most active derivatives are 1-[3(R)-(acetylthio) -3-substituted-benzoyl)-2(S)-methyl-propionyl]-L-prolines with an in vivo activity equivalent to SQ 14,225 (captopril). Structure-activity relationships are discussed. Changes in the configuration of the alpha-methyl group and the S-acetyl group affect the ACE activity. Coupling of 3-(substituted-benzoyl)-2-methylpropionic acids to L-proline via enol lactones is described.

  DOI：

  10.1021/jm00357a013