(3S,4S)-6-Chloro-1-(2-dimethylamino-ethyl)-3-ethyl-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one | 119217-43-5

• 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: (3S,4S)-6-Chloro-1-(2-dimethylamino-ethyl)-3-ethyl-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one
• 英文别名: (3S,4S)-6-chloro-1-[2-(dimethylamino)ethyl]-3-ethyl-4-(4-methoxyphenyl)-4,5-dihydro-3H-1-benzazepin-2-one
• CAS: 119217-43-5
• 化学式: C₂₃H₂₉ClN₂O₂
• 分子量: 400.948
• InChiKey: BFAHQOQQWVEOFN-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  dimethyl 2-[2-(2-chloro-6-nitrophenyl)-1-(4-methoxyphenyl)ethyl]propanedioate 在 吡啶 、 盐酸 、 sodium methylate 、 sodium hydride 、 tin(ll) chloride 、 lithium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.17h， 生成 (3S,4S)-6-Chloro-1-(2-dimethylamino-ethyl)-3-ethyl-4-(4-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one
  参考文献：
  名称：

  Benzazepinone calcium channel blockers. 3. Synthesis and structure-activity studies of 3-alkylbenzazepinones

  摘要：

  As part of a program aimed at identifying novel analogues of diltiazem, we developed several synthetic routes for 3-alkylbenzazepinones, both in racemic and nonracemic form. Structure-activity relationship studies in this series have led to identification of several analogues as potent calcium channel blocking agents, both in vitro and in vivo. Analogues containing a 6-trifluoromethyl substituent (17a and 17b) are the most potent vasorelaxants in vitro. The oral antihypertensive activity of these compounds is comparable to its 3-acetoxy derivative 1 (X = 6-CF3) and 8-chlorodiltiazem (2b). The 3-allyl analogue 17c is a more potent antihypertensive agent than 17a, 17b, or 8-chlorodiltiazem (2b), and has a longer duration of action in vivo.

  DOI：

  10.1021/jm00082a019

文献信息

• US4752645A
  申请人：——

  公开号：US4752645A

  公开（公告）日：1988-06-21
• Benzazepinone calcium channel blockers. 3. Synthesis and structure-activity studies of 3-alkylbenzazepinones
  作者：Jagabandhu Das、David M. Floyd、S. David Kimball、Keith J. Duff、Michael W. Lago、Robert V. Moquin、Ving G. Lee、Jack Z. Gougoutas、Vu Chi Truc

  DOI：10.1021/jm00082a019

  日期：1992.2

  As part of a program aimed at identifying novel analogues of diltiazem, we developed several synthetic routes for 3-alkylbenzazepinones, both in racemic and nonracemic form. Structure-activity relationship studies in this series have led to identification of several analogues as potent calcium channel blocking agents, both in vitro and in vivo. Analogues containing a 6-trifluoromethyl substituent (17a and 17b) are the most potent vasorelaxants in vitro. The oral antihypertensive activity of these compounds is comparable to its 3-acetoxy derivative 1 (X = 6-CF3) and 8-chlorodiltiazem (2b). The 3-allyl analogue 17c is a more potent antihypertensive agent than 17a, 17b, or 8-chlorodiltiazem (2b), and has a longer duration of action in vivo.