(3S,4R)-4-(4-Methoxy-phenyl)-2-oxo-3-propyl-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester | 138573-60-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,4R)-4-(4-Methoxy-phenyl)-2-oxo-3-propyl-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester
• CAS: 138573-60-1
• 化学式: C₂₃H₂₄F₃NO₄
• 分子量: 435.443
• InChiKey: FFTKTMVESPYMGX-GCJKJVERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-(4-Methoxy-phenyl)-2-oxo-3-propyl-7-trifluoromethyl-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 (3R,4S)-1-(2-Dimethylamino-ethyl)-4-(4-methoxy-phenyl)-3-propyl-7-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：

  2-[1-(4-Methoxy-phenyl)-2-(2-nitro-5-trifluoromethyl-phenyl)-ethyl]-2-propyl-malonic acid dimethyl ester 在 盐酸 、 sodium methylate 、 tin(ll) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (3S,4R)-4-(4-Methoxy-phenyl)-2-oxo-3-propyl-7-trifluoromethyl-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