N-benzyl 2-(hydroxyimino)-2-(isoquinolin-1-yl)acetamide | 1379796-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-benzyl 2-(hydroxyimino)-2-(isoquinolin-1-yl)acetamide
• CAS: 1379796-40-3
• 化学式: C₁₈H₁₅N₃O₂
• 分子量: 305.336
• InChiKey: KXOBFNBSEBDSRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.58
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-benzyl 2-(hydroxyimino)-2-(isoquinolin-1-yl)acetamide 在 甲酸铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以21%的产率得到(RS)-N-benzyl 2-amino-2-(isoquinolin-1-yl)acetamide
  参考文献：
  名称：

  Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

  摘要：

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.002
• 作为产物：
  描述：

  异喹啉-N-氧化物 在 盐酸 、 水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 苯甲酰氯 、 溶剂黄146 、 potassium hydroxide 、 sodium nitrite 作用下， 以 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 N-benzyl 2-(hydroxyimino)-2-(isoquinolin-1-yl)acetamide
  参考文献：
  名称：

  Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

  摘要：

  N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero) aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.002