N-(1-(4-chlorophenethyl)piperidin-4-yl)-6-chloro-2-methoxyacridin-9-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(1-(4-chlorophenethyl)piperidin-4-yl)-6-chloro-2-methoxyacridin-9-amine
• 英文别名: 6-chloro-N-[1-[2-(4-chlorophenyl)ethyl]piperidin-4-yl]-2-methoxyacridin-9-amine
• 化学式: C₂₇H₂₇Cl₂N₃O
• 分子量: 480.437
• InChiKey: NGGLCYCUEBMGRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-氯苯基)氯乙烷 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯酚 为溶剂， 反应 4.0h， 生成 N-(1-(4-chlorophenethyl)piperidin-4-yl)-6-chloro-2-methoxyacridin-9-amine
  参考文献：
  名称：

  Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species

  摘要：

  The in vitro neuronal cell death model based on the HT22 mouse hippocampal cell model is a convenient means of identifying compounds that protect against oxidative glutamate toxicity which plays a role in the development of certain neurodegenerative diseases. Functionalized acridin-9-yl-phenylamines were found to protect HT22 cells from glutamate challenge at submicromolar concentrations. The Aryl(1)-NH-Aryl(2) scaffold that is embedded in these compounds was the minimal pharmacophore for activity. Mechanistically, protection against the endogenous oxidative stress generated by glutamate did not involve up-regulation of glutathione levels but attenuation of the late stage increases in mitochondrial ROS and intracellular calcium levels. The NH residue in the pharmacophore played a crucial role in this regard as seen from the loss of neuroprotection when it was structurally modified or replaced. That the same NH was essential for radical scavenging in cell-free and cell-based systems pointed to an antioxidant basis for the neuroprotective activities of these compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.006