1-[3-bromo-3-(4-tert-butylbenzoyl)propionyl]-L-proline | 75381-53-2

• 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: 1-[3-bromo-3-(4-tert-butylbenzoyl)propionyl]-L-proline
• 英文别名: (2S)-1-[3-bromo-4-(4-tert-butylphenyl)-4-oxobutanoyl]pyrrolidine-2-carboxylic acid
• CAS: 75381-53-2
• 化学式: C₁₉H₂₄BrNO₄
• 分子量: 410.308
• InChiKey: IMOKSCGJXKXDHQ-LOACHALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[3-bromo-3-(4-tert-butylbenzoyl)propionyl]-L-proline 、 potassium thioacetate 以 乙醇 为溶剂， 反应 18.0h， 以95%的产率得到1-[3-Acetylthio-3-(4-tert-butylbenzoyl)propionyl]-L-proline
  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
• 作为产物：
  描述：

  1-[3-(4-tert-butylbenzoyl)propionyl]-L-proline 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 1-[3-bromo-3-(4-tert-butylbenzoyl)propionyl]-L-proline
  参考文献：
  名称：

  Substituted thio-substituted benzyl-propionyl-L-prolines

  摘要：

  这份披露描述了新型的取代的ω-芳酰基（丙酰基或丁酰基）-L-脯氨酸及其酯和阳离子盐，它们在哺乳动物中作为降血压剂是有用的。

  公开号：

  US04226775A1

文献信息

• Novel substituted omega-aroyl(propionyl or butyryl)-L-prolines, pharmaceutical compositions containing them and processes for their preparation
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0010347B1

  公开（公告）日：1983-11-09
• US4226775A
  申请人：——

  公开号：US4226775A

  公开（公告）日：1980-10-07
• Substituted thio-substituted benzyl-propionyl-L-prolines
  申请人：American Cyanamid Company

  公开号：US04226775A1

  公开（公告）日：1980-10-07

  This disclosure describes novel substituted .omega.-aroyl(propionyl or butyryl)-L-prolines and the esters and cationic salts thereof which are useful as hypotensive agents in mammals.

  这份披露描述了新型的取代的ω-芳酰基（丙酰基或丁酰基）-L-脯氨酸及其酯和阳离子盐，它们在哺乳动物中作为降血压剂是有用的。
• Antihypertensive agents: angiotensin converting enzyme inhibitors. 1-[3-(Acylthio)-3-aroylpropionyl]-L-prolines
  作者：Francis J. McEvoy、Fong M. Lai、J. Donald Albright

  DOI：10.1021/jm00357a013

  日期：1983.3

  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.