4-carbamoyl-1-(2-hydroxybenzyl)piperidinium chloride | 1422063-93-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-carbamoyl-1-(2-hydroxybenzyl)piperidinium chloride
• 英文别名: 4-Carbamoyl-1-(2-hydroxybenzyl)piperidinium chloride；1-[(2-hydroxyphenyl)methyl]piperidin-1-ium-4-carboxamide;chloride
• CAS: 1422063-93-1
• 化学式: C₁₃H₁₈N₂O₂*ClH
• 分子量: 270.759
• InChiKey: GNDSGXXXTBTKNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  水杨醇 、 4-哌啶甲酰胺盐酸盐 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以58.7%的产率得到4-carbamoyl-1-(2-hydroxybenzyl)piperidinium chloride
  参考文献：
  名称：

  Bioisosteric synthesis of nitrogen containing derivatives of salicyl alcohol, their in vivo pharmacological studies with molecular modeling

  摘要：

  Starting with salicylaldehyde, compounds (I) [1-(2-hydroxybenzyl)piperidinium chloride] and (II) [4-carbamoyl-1-(2-hydroxybenzyl)piperidinium chloride] were prepared via multi step synthesis. The synthesized compounds were evaluated in vivo for their anti-inflammatory, analgesic, and anti-pyretic activities. Both compounds showed significant pharmacological profile when compared with reference standard, aspirin. In an attempt to understand the ligand-protein interaction in terms of the binding affinity, the synthetic molecule II was subjected to docking analysis using AutoDock which showed better binding modes with the active sites of COX's enzymes.

  DOI：

  10.1007/s00044-013-0473-z