(cis)-1-[2-(Dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-3-(2-propenyl)-6-(trifluoromethyl)2H-1-benzazepin-2-one | 111604-75-2

• 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: (cis)-1-[2-(Dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-3-(2-propenyl)-6-(trifluoromethyl)2H-1-benzazepin-2-one
• 英文别名: (3R,4R)-1-[2-(dimethylamino)ethyl]-4-(4-methoxyphenyl)-3-prop-2-enyl-6-(trifluoromethyl)-4,5-dihydro-3H-1-benzazepin-2-one
• CAS: 111604-75-2
• 化学式: C₂₅H₂₉F₃N₂O₂
• 分子量: 446.513
• InChiKey: NNPLWRUDJVFIJN-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (cis)-1-[2-(Dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-3-(2-propenyl)-6-(trifluoromethyl)2H-1-benzazepin-2-one 在 palladium on charcoal 作用下， 以 乙酸乙酯 为溶剂， 生成 1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-3-propyl-6-(trifluoromethyl)-2H-1-benzazepin-2-one
  参考文献：
  名称：

  Benzazepine derivatives

  摘要：

  具有如下式子##STR1##和其药学上可接受的盐，表现出扩张血管的活性。

  公开号：

  US04752645A1
• 作为产物：
  描述：

  (3S,4S-trans)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one 在 硫酸 、 对氨基苯酚 、 sodium hydride 、 lithium bromide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.92h， 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
  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

• DAS, JAGABANDHU;FLOYD, SQUARE DAVID;KRAPCHO, JOHN
  作者：DAS, JAGABANDHU、FLOYD, SQUARE DAVID、KRAPCHO, JOHN

  DOI：——

  日期：——
• US4752645A
  申请人：——

  公开号：US4752645A

  公开（公告）日：1988-06-21
• Benzazepine derivatives
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04752645A1

  公开（公告）日：1988-06-21

  Vasodilating activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.

  具有如下式子##STR1##和其药学上可接受的盐，表现出扩张血管的活性。
• 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.