2-[1-(4-Methoxy-phenyl)-2-(2-nitro-5-trifluoromethyl-phenyl)-ethyl]-2-propyl-malonic acid dimethyl ester | 138573-34-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[1-(4-Methoxy-phenyl)-2-(2-nitro-5-trifluoromethyl-phenyl)-ethyl]-2-propyl-malonic acid dimethyl ester
• 英文别名: dimethyl 2-[1-(4-methoxyphenyl)-2-[2-nitro-5-(trifluoromethyl)phenyl]ethyl]-2-propylpropanedioate
• CAS: 138573-34-9
• 化学式: C₂₄H₂₆F₃NO₇
• 分子量: 497.468
• InChiKey: SLBZEYCCBKJESQ-UHFFFAOYSA-N

物化性质

• 沸点：
  542.7±50.0 °C(predicted)
• 密度：
  1.268±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  104.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-[1-(4-Methoxy-phenyl)-2-(2-nitro-5-trifluoromethyl-phenyl)-ethyl]-2-propyl-malonic acid dimethyl ester 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 16.33h， 生成 (3S,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-(5-trifluoromethyl-2-nitrophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid,dimethyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 生成 2-[1-(4-Methoxy-phenyl)-2-(2-nitro-5-trifluoromethyl-phenyl)-ethyl]-2-propyl-malonic acid dimethyl 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