N,N-Bis-<2-chlor-aethyl>-N'-acetyl-m-phenylendiamin | 13686-20-9

• 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: N,N-Bis-<2-chlor-aethyl>-N'-acetyl-m-phenylendiamin
• 英文别名: N,N-bis(2-chloroethyl)-3-acetamidoaniline；N-[3-[bis(2-chloroethyl)amino]phenyl]acetamide
• CAS: 13686-20-9
• 化学式: C₁₂H₁₆Cl₂N₂O
• 分子量: 275.178
• InChiKey: CLOVZCAYWFLWIW-UHFFFAOYSA-N

物化性质

• 沸点：
  467.1±40.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吲哚啉 、 N,N-Bis-<2-chlor-aethyl>-N'-acetyl-m-phenylendiamin 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以32%的产率得到4'-(3-acetamidophenyl)spiro[indoline-1,1'-piperazin]-1-ium chloride
  参考文献：
  名称：

  Synthesis and structure–analgesic activity relationships of a novel series of monospirocyclopiperazinium salts (MSPZ)

  摘要：

  A series of monospirocyclopiperazinium salts were designed and synthesized to search for a peripherally-acting analgesic drug with low side effects. Extensive SAR studies revealed that a suitable (NRR3)-R-2 was critical for the analgesic activity, which might be beneficial to expose the cationic nitrogen to bind to the receptor, and possibly interact with the receptor via pi-pi interaction. Introduction of substituting group on the N-4-phenyl ring could improve the activity, and the best position was the 4-position. Compound 14n showed more potent analgesic activity (63%, 20 mu M/kg, sc) and holds promise for development as a mechanically new analgesic drug. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.052
• 作为产物：
  描述：

  间氨基乙酰苯胺 在 三乙胺 、 calcium carbonate 、 potassium iodide 、 sodium chloride 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.33h， 生成 N,N-Bis-<2-chlor-aethyl>-N'-acetyl-m-phenylendiamin
  参考文献：
  名称：

  Synthesis and structure–analgesic activity relationships of a novel series of monospirocyclopiperazinium salts (MSPZ)

  摘要：

  A series of monospirocyclopiperazinium salts were designed and synthesized to search for a peripherally-acting analgesic drug with low side effects. Extensive SAR studies revealed that a suitable (NRR3)-R-2 was critical for the analgesic activity, which might be beneficial to expose the cationic nitrogen to bind to the receptor, and possibly interact with the receptor via pi-pi interaction. Introduction of substituting group on the N-4-phenyl ring could improve the activity, and the best position was the 4-position. Compound 14n showed more potent analgesic activity (63%, 20 mu M/kg, sc) and holds promise for development as a mechanically new analgesic drug. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.052

文献信息

• Synthesis and structure–analgesic activity relationships of a novel series of monospirocyclopiperazinium salts (MSPZ)
  作者：Song-Wen Lin、Qi Sun、Ze-Mei Ge、Xin Wang、Jia Ye、Run-Tao Li

  DOI：10.1016/j.bmcl.2010.12.052

  日期：2011.2

  A series of monospirocyclopiperazinium salts were designed and synthesized to search for a peripherally-acting analgesic drug with low side effects. Extensive SAR studies revealed that a suitable (NRR3)-R-2 was critical for the analgesic activity, which might be beneficial to expose the cationic nitrogen to bind to the receptor, and possibly interact with the receptor via pi-pi interaction. Introduction of substituting group on the N-4-phenyl ring could improve the activity, and the best position was the 4-position. Compound 14n showed more potent analgesic activity (63%, 20 mu M/kg, sc) and holds promise for development as a mechanically new analgesic drug. (C) 2010 Elsevier Ltd. All rights reserved.