Acetic acid (3R,4S)-6-chloro-4-(4-methoxy-phenyl)-2-oxo-1-(S)-1-pyrrolidin-2-ylmethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl ester | 128509-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: Acetic acid (3R,4S)-6-chloro-4-(4-methoxy-phenyl)-2-oxo-1-(S)-1-pyrrolidin-2-ylmethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl ester
• 英文别名: [(3R,4S)-6-chloro-4-(4-methoxyphenyl)-2-oxo-1-[[(2S)-pyrrolidin-2-yl]methyl]-4,5-dihydro-3H-1-benzazepin-3-yl] acetate
• CAS: 128509-83-1
• 化学式: C₂₄H₂₇ClN₂O₄
• 分子量: 442.942
• InChiKey: UEHOEMTYJSJMSO-WCAVRKLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl (2S)-2-[[(3R,4S)-3-acetyloxy-6-chloro-4-(4-methoxyphenyl)-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]methyl]pyrrolidine-1-carboxylate 生成 Acetic acid (3R,4S)-6-chloro-4-(4-methoxy-phenyl)-2-oxo-1-(S)-1-pyrrolidin-2-ylmethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl ester
  参考文献：
  名称：

  FLOYD, DAVID M.;HUNT, JOHN T.;KIMBALL, SPENCER D.;KRAPCHO, JOHN;DAS, JAGA+

  摘要：

  DOI：

文献信息

• Benzazepinone calcium channel blockers. 5. Effects on antihypertensive activity associated with N1 and aromatic substituents
  作者：Jagabandhu Das、David M. Floyd、S. David Kimball、Keith J. Duff、Michael W. Lago、John Krapcho、Ronald E. White、Richard E. Ridgewell、Mary T. Obermeier

  DOI：10.1021/jm00092a011

  日期：1992.7

  We have shown that the pyrrolidinylmethyl substituent on the lactam nitrogen (Nl) of benzazepinone and benzothiazepinone calcium channel blocking agents is resistant to metabolic deamination and generally increases the duration and potency of antihypertensive activity in spontaneously hypertensive rats (SHR) relative to (N,N-dimethylamino) ethyl analogs. Additionally, compounds possessing a substituent on the fused aromatic ring are more resistant to metabolic deacylation of the C3 hydroxy function, which may explain why aromatic substituents also frequently increase the potency and/or duration of antihypertensive activity. Our data also indicate the in antihypertensive activity associated with these structural modifications is independent of any effects of potency in vitro. Overall, we interpret these results to indicate that these structural modifications improve antihypertensive activity as a result of increased metabolic stability and, consequently, oral bioavailability.
• FLOYD, DAVID M.;HUNT, JOHN T.;KIMBALL, SPENCER D.;KRAPCHO, JOHN;DAS, JAGA+
  作者：FLOYD, DAVID M.、HUNT, JOHN T.、KIMBALL, SPENCER D.、KRAPCHO, JOHN、DAS, JAGA+

  DOI：——

  日期：——