[(3-Acetylsulfanyl-2-methyl-propionyl)-((1S,2R,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-amino]-acetic acid | 78773-58-7

• 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: [(3-Acetylsulfanyl-2-methyl-propionyl)-((1S,2R,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-amino]-acetic acid
• CAS: 78773-58-7
• 化学式: C₁₉H₃₁NO₄S
• 分子量: 369.525
• InChiKey: SLKDSLAWMQSCJY-QJVFPXCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  74.68
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(3-Acetylsulfanyl-2-methyl-propionyl)-((1S,2R,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-amino]-acetic acid 在 氨 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以87%的产率得到[(3-Mercapto-2-methyl-propionyl)-((1S,2R,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-amino]-acetic acid
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives

  摘要：

  A variety of N-substituted (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo. The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds. A number of these compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model. One of the most active members of the series was (S)-N-cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1 -oxopropyl]glycine (REV 3659-(S), pivopril). Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00379a013
• 作为产物：
  描述：

  [(3-Acetylsulfanyl-2-methyl-propionyl)-((1S,2R,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-amino]-acetic acid tert-butyl ester 在 三氟乙酸 作用下， 以 various solvent(s) 为溶剂， 反应 1.5h， 以77%的产率得到[(3-Acetylsulfanyl-2-methyl-propionyl)-((1S,2R,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-amino]-acetic acid
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives

  摘要：

  A variety of N-substituted (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo. The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds. A number of these compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model. One of the most active members of the series was (S)-N-cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1 -oxopropyl]glycine (REV 3659-(S), pivopril). Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00379a013