4'-(3-hydroxyphenyl)spiro[indoline-1,1'-piperazin]-1-ium chloride | 1268821-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4'-(3-hydroxyphenyl)spiro[indoline-1,1'-piperazin]-1-ium chloride
• 英文别名: 3-Spiro[1,4-diazinan-4-ium-4,1'-2,3-dihydroindol-1-ium]-1-ylphenol;chloride
• CAS: 1268821-34-6
• 化学式: C₁₈H₂₁N₂O*Cl
• 分子量: 316.831
• InChiKey: DUDXVBCCECMMEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苄氧基苯胺 在 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 三乙胺 、 calcium carbonate 、 potassium iodide 、 sodium chloride 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~160.0 ℃ 、405.33 kPa 条件下， 反应 67.33h， 生成 4'-(3-hydroxyphenyl)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

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.