(3S,4S)-7-Bromo-6-methoxy-4-(4-methoxy-phenyl)-3-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester | 138573-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3S,4S)-7-Bromo-6-methoxy-4-(4-methoxy-phenyl)-3-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester
• 英文别名: (3S,4R)-7-Bromo-6-methoxy-4-(4-methoxy-phenyl)-3-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester
• CAS: 138573-53-2
• 化学式: C₂₁H₂₂BrNO₅
• 分子量: 448.313
• InChiKey: ZBIXAPBLIAJTAS-VFNWGFHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4S)-7-Bromo-6-methoxy-4-(4-methoxy-phenyl)-3-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester 在 吡啶 、 sodium hydride 、 lithium iodide 作用下， 反应 12.83h， 生成 (3S,4S)-7-Bromo-1-(2-dimethylamino-ethyl)-6-methoxy-4-(4-methoxy-phenyl)-3-methyl-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 2-[2-(6-amino-3-bromo-2-methoxyphenyl)-1-(4-methoxyphenyl)ethyl]-2-methylpropanedioate 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,4S)-7-Bromo-6-methoxy-4-(4-methoxy-phenyl)-3-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester
  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