3-Allyl-4-(4-methoxy-phenyl)-6-trifluoromethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one | 111605-03-9

• 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: 3-Allyl-4-(4-methoxy-phenyl)-6-trifluoromethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one
• 英文别名: 4-(4-Methoxyphenyl)-3-prop-2-enyl-6-(trifluoromethyl)-1,3,4,5-tetrahydro-1-benzazepin-2-one
• CAS: 111605-03-9
• 化学式: C₂₁H₂₀F₃NO₂
• 分子量: 375.391
• InChiKey: MNVXZAALCWFZAE-UHFFFAOYSA-N

物化性质

• 沸点：
  464.3±45.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Allyl-4-(4-methoxy-phenyl)-6-trifluoromethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one 、 2-氯-N,N-二甲基乙胺 在 sodium hydride 作用下， 生成 (cis)-1-[2-(Dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-3-(2-propenyl)-6-(trifluoromethyl)-2H-1-benzazepin-2-one 、 (3R,4S)-3-Allyl-1-(2-dimethylamino-ethyl)-4-(4-methoxy-phenyl)-6-trifluoromethyl-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
• 作为产物：
  描述：

  dimethyl <1-(4-methoxyphenyl)-2-<2-nitro-6-(trifluoromethyl)phenyl>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 16.83h， 生成 3-Allyl-4-(4-methoxy-phenyl)-6-trifluoromethyl-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

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

  公开号：EP0229329A1

  公开（公告）日：1987-07-22

  Vasodilating activity is exhibited by compounds having the formula and pharmaceutically acceptable salts thereof.

  具有以下式子的化合物具有血管扩张活性 及其药学上可接受的盐类。
• 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.