cinnamoylcholine chloride

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: cinnamoylcholine chloride
• 英文别名: Trimethyl-[2-(3-phenylprop-2-enoyloxy)ethyl]azanium;chloride
• 化学式: C₁₄H₂₀NO₂*Cl
• 分子量: 269.771
• InChiKey: IYWKYXCCOWGFIW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.05
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cinnamoylcholine chloride 以 水 为溶剂， 生成
  参考文献：
  名称：

  Studien zum vorgang der wasserstoffübertragung 23 modellversuche zur wirkungsweise der leitsalze bei elektrochemischen reduktionen

  摘要：

  DOI：

  10.1016/s0040-4039(01)98345-5
• 作为产物：
  描述：

  氯化胆碱 在 氯化亚砜 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 45.17h， 生成 cinnamoylcholine chloride
  参考文献：
  名称：

  Bifunctional phenolic-choline conjugates as anti-oxidants and acetylcholinesterase inhibitors

  摘要：

  Because of the complex cascade of molecular events that can occur in the brain of an Alzheimer's disease (AD) patient, the therapy of this neurodegenerative disease seems more likely to be achieved by multifunctional drugs. Herein, a new series of dual-targeting ligands have been developed and in vitro bioevaluated. Their architecture is based on conjugating the acetylcholinesterase inhibition and anti-oxidant properties in one molecular entity. Specifically, a series of naturally occurring phenolic acids with recognized anti-oxidant properties (derivatives of caffeic acid, rosmarinic acid, and trolox) have been conjugated with choline to account for the recognition by acetylcholinesterase (AChE). The synthesized hybrid compounds evidenced AChE inhibitory capacity of micromolar range (rationalized by molecular modeling studies) and good antioxidant properties. Their effects on human neuroblastoma cells, previously treated with beta-amyloid peptides and 1-methyl-4-phenylpyridinium ion neurotoxins (to simulate AD and Parkinson's disease, respectively), also demonstrated a considerable capacity for protection against the cytotoxicity of these stressors.

  DOI：

  10.3109/14756366.2010.529806

文献信息

• Bifunctional phenolic-choline conjugates as anti-oxidants and acetylcholinesterase inhibitors
  作者：Jaroslav Šebestík、Sérgio M. Marques、Pedro L. Falé、Susana Santos、Daniela M. Arduíno、Sandra M. Cardoso、Catarina R. Oliveira、M. Luísa M. Serralheiro、M. Amélia Santos

  DOI：10.3109/14756366.2010.529806

  日期：2011.8.1

  Because of the complex cascade of molecular events that can occur in the brain of an Alzheimer's disease (AD) patient, the therapy of this neurodegenerative disease seems more likely to be achieved by multifunctional drugs. Herein, a new series of dual-targeting ligands have been developed and in vitro bioevaluated. Their architecture is based on conjugating the acetylcholinesterase inhibition and anti-oxidant properties in one molecular entity. Specifically, a series of naturally occurring phenolic acids with recognized anti-oxidant properties (derivatives of caffeic acid, rosmarinic acid, and trolox) have been conjugated with choline to account for the recognition by acetylcholinesterase (AChE). The synthesized hybrid compounds evidenced AChE inhibitory capacity of micromolar range (rationalized by molecular modeling studies) and good antioxidant properties. Their effects on human neuroblastoma cells, previously treated with beta-amyloid peptides and 1-methyl-4-phenylpyridinium ion neurotoxins (to simulate AD and Parkinson's disease, respectively), also demonstrated a considerable capacity for protection against the cytotoxicity of these stressors.
• Studien zum vorgang der wasserstoffübertragung 23 modellversuche zur wirkungsweise der leitsalze bei elektrochemischen reduktionen
  作者：L. Horner、H.D. Ruprecht

  DOI：10.1016/s0040-4039(01)98345-5

  日期：1970.1