6-{2'-fluoro-4'-[1-oxo-1-(2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethylamino)propan-2-yl]biphenyl-4-yloxy}hexyl nitrate | 1435359-65-1

• 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: 6-{2'-fluoro-4'-[1-oxo-1-(2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethylamino)propan-2-yl]biphenyl-4-yloxy}hexyl nitrate
• 英文别名: 6-[4-[2-Fluoro-4-[1-oxo-1-[2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethylamino]propan-2-yl]phenyl]phenoxy]hexyl nitrate；6-[4-[2-fluoro-4-[1-oxo-1-[2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethylamino]propan-2-yl]phenyl]phenoxy]hexyl nitrate
• CAS: 1435359-65-1
• 化学式: C₃₆H₄₁FN₄O₅
• 分子量: 628.744
• InChiKey: FBWXOUBMHZMKRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  氟比洛芬 在 aluminum (III) chloride 、 lithium hydroxide monohydrate 、 硫酸 、 水 、 potassium carbonate 、 silver nitrate 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 110.5h， 生成 6-{2'-fluoro-4'-[1-oxo-1-(2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethylamino)propan-2-yl]biphenyl-4-yloxy}hexyl nitrate
  参考文献：
  名称：

  NO-donating tacrine derivatives as potential butyrylcholinesterase inhibitors with vasorelaxation activity

  摘要：

  To search for potent anti-Alzheimer's disease (AD) agents with multifunctional effects, 12 NO-donating tacrine-flurbiprofen hybrid compounds (2a-l) were synthesized and biologically evaluated. It was found that all the new target compounds showed selective butyrylcholinesterase (BuChE) inhibitory activity in vitro comparable or higher than tacrine and the tacrine-flurbiprofen hybrid compounds 1a-c, and released moderate amount of NO in vitro. The kinetic study suggests that one of the most active and highest BuChE selective compounds 2d may not only compete with the substrate for the same catalytic active site (CAS) but also interact with a second binding site. Furthermore, 2d and 2l exhibited significant vascular relaxation effect, which is beneficial for the treatment of AD. All the results suggest that 2d and 2l might be promising lead compounds for further research. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.008

文献信息

• NO-donating tacrine derivatives as potential butyrylcholinesterase inhibitors with vasorelaxation activity
  作者：Yao Chen、Jianfei Sun、Zhangjian Huang、Hong Liao、Sixun Peng、Jochen Lehmann、Yihua Zhang

  DOI：10.1016/j.bmcl.2013.04.008

  日期：2013.6

  To search for potent anti-Alzheimer's disease (AD) agents with multifunctional effects, 12 NO-donating tacrine-flurbiprofen hybrid compounds (2a-l) were synthesized and biologically evaluated. It was found that all the new target compounds showed selective butyrylcholinesterase (BuChE) inhibitory activity in vitro comparable or higher than tacrine and the tacrine-flurbiprofen hybrid compounds 1a-c, and released moderate amount of NO in vitro. The kinetic study suggests that one of the most active and highest BuChE selective compounds 2d may not only compete with the substrate for the same catalytic active site (CAS) but also interact with a second binding site. Furthermore, 2d and 2l exhibited significant vascular relaxation effect, which is beneficial for the treatment of AD. All the results suggest that 2d and 2l might be promising lead compounds for further research. (C) 2013 Elsevier Ltd. All rights reserved.