[4-(2-Amino-propyl)-3,5-difluoro-phenyl]-benzyl-methyl-amine | 226411-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4-(2-Amino-propyl)-3,5-difluoro-phenyl]-benzyl-methyl-amine
• CAS: 226411-12-7
• 化学式: C₁₇H₂₀F₂N₂
• 分子量: 290.356
• InChiKey: ASSKFGXFZWIDIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [4-(2-Amino-propyl)-3,5-difluoro-phenyl]-benzyl-methyl-amine 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 N'-<1-(4-methylamino-2,6-difluorophenyl)-2-propyl>glycinamide acetate
  参考文献：
  名称：

  Prodrugs of neuron-selective monoamine oxidase inhibitors: amino acid derivatives of 1-(4-aminophenyl)-2-aminopropanes

  摘要：

  Six amino acid derivatives of 1-(4-aminophenyl)-2-aminopropanes and their parent amines were synthezised and tested for their potency and selectivity in inhibiting monoamine oxidase (MAO) in vitro and in vivo. The amino acid derivatives were 300-1000 times less potent than the parent amines in inhibiting the MAO-A activity in a rat brain mitochondrial preparation in vitro. All compounds, except the (R)-valinamide derivative (22), were potent inhibitors of MAO in the rat brain in vivo and were, like the parent amines markedly more potent within the monoaminergic neurons than in other neurons. The glycinamide derivative 7 showed the largest difference between intra- and extra-neuronal inhibition in serotonergic neurons. The time course of the inhibitory effect of 7 in vivo showed that it is a reversible inhibitor with a long duration. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80047-6
• 作为产物：
  描述：

  N-(3,5-二氟-苯基)-甲酰胺 在 lithium aluminium tetrahydride 、 正丁基锂 、 ammonium acetate 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 [4-(2-Amino-propyl)-3,5-difluoro-phenyl]-benzyl-methyl-amine
  参考文献：
  名称：

  Prodrugs of neuron-selective monoamine oxidase inhibitors: amino acid derivatives of 1-(4-aminophenyl)-2-aminopropanes

  摘要：

  Six amino acid derivatives of 1-(4-aminophenyl)-2-aminopropanes and their parent amines were synthezised and tested for their potency and selectivity in inhibiting monoamine oxidase (MAO) in vitro and in vivo. The amino acid derivatives were 300-1000 times less potent than the parent amines in inhibiting the MAO-A activity in a rat brain mitochondrial preparation in vitro. All compounds, except the (R)-valinamide derivative (22), were potent inhibitors of MAO in the rat brain in vivo and were, like the parent amines markedly more potent within the monoaminergic neurons than in other neurons. The glycinamide derivative 7 showed the largest difference between intra- and extra-neuronal inhibition in serotonergic neurons. The time course of the inhibitory effect of 7 in vivo showed that it is a reversible inhibitor with a long duration. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80047-6