1-(2-(2,4-difluorobenzoyl)pyrrolidin-1-yl)ethanone | 1620495-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(2,4-difluorobenzoyl)pyrrolidin-1-yl)ethanone
• CAS: 1620495-97-7
• 化学式: C₁₃H₁₃F₂NO₂
• 分子量: 253.249
• InChiKey: KDKGSDUDORWWGF-UHFFFAOYSA-N

物化性质

• 熔点：
  60-62 °C
• 沸点：
  394.8±42.0 °C(predicted)
• 密度：
  1.289±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(2-(2,4-difluorobenzoyl)pyrrolidin-1-yl)ethanone 在 硫酸羟胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 50.0h， 生成 (5-amino-3-(pyrazin-2-yl)-1,2,4-triazin-6-yl)(2-(6-fluorobenzo[d]isoxazol-3-yl)pyrrolidin-1-yl)methanone
  参考文献：
  名称：

  Design and synthesis of (5-amino-1, 2, 4-triazin-6-yl)(2-(benzo[d] isoxazol-3-yl) pyrrolidin-1-yl)methanone derivatives as sodium channel blocker and anticonvulsant agents

  摘要：

  A series of novel (5-amino-3-substituted-1, 2, 4-triazin-6-yl) (2-(6-halo-substituted benzo[d]isoxazol-3-yl) pyrrolidin-1-yl) methanone 5a-5r was synthesized. Their anticonvulsant activities were evaluated by the maximal electroshock (MES) test and neurotoxicity was evaluated by the rotorod test. The MES test showed that (5-amino-3-phenyl-1, 2, 4-triazin-6-yl)(2-(6-fluorobenzo[d]isoxazol-3-yl) pyrrolidin-1-yl) methanone 5c was found to be the most potent compound with ED50 value of 6.20 mg/kg (oral/rat) and a protective index (PI = ED50/TD50) value of >48.38, which was much higher than the PI of the reference drug phenytoin. To explain the possible mechanism of action of selected derivatives 5 b, 5 c, 5 i and 5 o, their influence on sodium channel was evaluated in vitro.

  DOI：

  10.3109/14756366.2013.815177
• 作为产物：
  描述：

  N-Acetyl-DL-prolin 在 aluminum (III) chloride 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-(2-(2,4-difluorobenzoyl)pyrrolidin-1-yl)ethanone
  参考文献：
  名称：

  Design and synthesis of (5-amino-1, 2, 4-triazin-6-yl)(2-(benzo[d] isoxazol-3-yl) pyrrolidin-1-yl)methanone derivatives as sodium channel blocker and anticonvulsant agents

  摘要：

  A series of novel (5-amino-3-substituted-1, 2, 4-triazin-6-yl) (2-(6-halo-substituted benzo[d]isoxazol-3-yl) pyrrolidin-1-yl) methanone 5a-5r was synthesized. Their anticonvulsant activities were evaluated by the maximal electroshock (MES) test and neurotoxicity was evaluated by the rotorod test. The MES test showed that (5-amino-3-phenyl-1, 2, 4-triazin-6-yl)(2-(6-fluorobenzo[d]isoxazol-3-yl) pyrrolidin-1-yl) methanone 5c was found to be the most potent compound with ED50 value of 6.20 mg/kg (oral/rat) and a protective index (PI = ED50/TD50) value of >48.38, which was much higher than the PI of the reference drug phenytoin. To explain the possible mechanism of action of selected derivatives 5 b, 5 c, 5 i and 5 o, their influence on sodium channel was evaluated in vitro.

  DOI：

  10.3109/14756366.2013.815177