1-(4-(8-bromooctyloxy)benzyl)piperidine | 913380-93-5

• 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: 1-(4-(8-bromooctyloxy)benzyl)piperidine
• 英文别名: 1-[[4-(8-Bromooctoxy)phenyl]methyl]piperidine
• CAS: 913380-93-5
• 化学式: C₂₀H₃₂BrNO
• 分子量: 382.384
• InChiKey: CDXPQLTYKCZKQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-(8-bromooctyloxy)benzyl)piperidine 、 N-去甲基加兰它敏氢溴酸盐 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以53.4%的产率得到10-N-demethyl-10-N-(8-(4-(piperidin-1-ylmethyl)phenoxy)octan-1-yl)galanthamine
  参考文献：
  名称：

  Design, synthesis and evaluation of galanthamine derivatives as acetylcholinesterase inhibitors

  摘要：

  A new series of galanthamine derivatives have been designed, synthesized and evaluated as acetylcholinesterase inhibitors. All of the new compounds prepared showed high AChE inhibitory activities, with compound 3e that has an N-hexyl-benzyl piperidine substituent on the nitrogen atom reaching the best inhibitory activity for AChE (IC50 = 5.62 nM). The docking study performed with AutoDock demonstrated that 3e was nicely accommodated by AChE. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.018
• 作为产物：
  描述：

  4-(哌啶-1-基甲基)苯酚 、 1,8-二溴辛烷 在 sodium hydroxide 、 十六烷基三甲基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以90.3%的产率得到1-(4-(8-bromooctyloxy)benzyl)piperidine
  参考文献：
  名称：

  Design, synthesis and evaluation of galanthamine derivatives as acetylcholinesterase inhibitors

  摘要：

  A new series of galanthamine derivatives have been designed, synthesized and evaluated as acetylcholinesterase inhibitors. All of the new compounds prepared showed high AChE inhibitory activities, with compound 3e that has an N-hexyl-benzyl piperidine substituent on the nitrogen atom reaching the best inhibitory activity for AChE (IC50 = 5.62 nM). The docking study performed with AutoDock demonstrated that 3e was nicely accommodated by AChE. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.018

文献信息

• Design, Synthesis and Evaluation of Difunctionalized 4-Hydroxybenzaldehyde Derivatives as Novel Cholinesterase Inhibitors
  作者：Liang Yu、Rihui Cao、Wei Yi、Qin Yan、Zhiyong Chen、Lin Ma、Huacan Song

  DOI：10.1248/cpb.58.1216

  日期：——

  A series of difunctionalized 4-hydroxybenzaldehyde derivatives were designed, synthesized and evaluated as cholinesterase (acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)) inhibitors. The results demonstrated that all the compounds had more potent AChE and BChE inhibitory activities than galanthamine-HBr, one of the best cholinesterase inhibitors known so far. The inhibition mechanism revealed that the best active compound 4e displayed a mix-type mode of AChE and BChE by its dual-site interactions with the catalytic triad active center and the peripheral anionic site (PAS) of enzyme. All these data suggested that further development of such compounds may be of interest.

  设计、合成了一系列双官能化4-羟基苯甲醛衍生物，并作为胆碱酯酶（乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE））抑制剂进行了评估。结果表明，所有化合物均比加兰他敏-HBr（迄今为止已知的最好的胆碱酯酶抑制剂之一）具有更有效的 AChE 和 BChE 抑制活性。抑制机制表明，最佳活性化合物4e通过与酶的催化三联体活性中心和外周阴离子位点（PAS）的双位点相互作用，表现出AChE和BChE的混合型模式。所有这些数据表明，此类化合物的进一步开发可能值得关注。