(3R-cis)-3-(acetyloxy)-1-<2-(dimethylamino)ethyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one | 142234-89-7

• 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: (3R-cis)-3-(acetyloxy)-1-<2-(dimethylamino)ethyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one
• 英文别名: (cis)-3-(acetyloxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one；Acetic acid 1-(2-dimethylamino-ethyl)-4-(4-methoxy-phenyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl ester；[(3R,4S)-1-[2-(dimethylamino)ethyl]-4-(4-methoxyphenyl)-2-oxo-4,5-dihydro-3H-1-benzazepin-3-yl] acetate
• CAS: 142234-89-7
• 化学式: C₂₃H₂₈N₂O₄
• 分子量: 396.486
• InChiKey: XBMWQRZMZDCXNK-RBBKRZOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3R-cis)-3-(acetyloxy)-7-chloro-1-<2-(dimethylamino)ethyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 (3R-cis)-3-(acetyloxy)-1-<2-(dimethylamino)ethyl>-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one
  参考文献：
  名称：

  Benzazepinone calcium channel blockers. 5. Effects on antihypertensive activity associated with N1 and aromatic substituents

  摘要：

  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.

  DOI：

  10.1021/jm00092a011

文献信息

• Benzazepine derivatives
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0205334A2

  公开（公告）日：1986-12-17

  Vasodilating activity is exhibited by new compounds having the formula and pharmaceutically acceptable salts thereof, wherein R1, R2, R3. R4. R5 and n are as defined herein.

  具有以下式子的新化合物具有血管扩张活性 及其药学上可接受的盐类，其中 R1、R2、R3.R4.R5 和 n 如本文所定义。
• US4748239A
  申请人：——

  公开号：US4748239A

  公开（公告）日：1988-05-31