N-[4-(8-bromooctyloxy)benzyl]-N-ethylethanamine | 1234574-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-(8-bromooctyloxy)benzyl]-N-ethylethanamine
• 英文别名: N-[[4-(8-bromooctoxy)phenyl]methyl]-N-ethylethanamine
• CAS: 1234574-97-0
• 化学式: C₁₉H₃₂BrNO
• 分子量: 370.373
• InChiKey: FNZUASJNULCWIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  四氢吡咯 、 N-[4-(8-bromooctyloxy)benzyl]-N-ethylethanamine 在 potassium iodide 作用下， 以 乙醇 为溶剂， 以82%的产率得到N-ethyl-N-(4-(8-(pyrrolidin-1-yl)octyloxy)benzyl)ethanamine
  参考文献：
  名称：

  Synthesis of 4-[(diethylamino)methyl]-phenol derivatives as novel cholinesterase inhibitors with selectivity towards butyrylcholinesterase

  摘要：

  A series of novel cholinesterase inhibitors, being composed of 4-[(diethylamino) methyl]-phenoxy and secondary amine which were linked with a different length alkyl chain, were designed and synthesized from the starting material p-hydroxybenzaldehyde. These compounds were evaluated as acetylcholinesterase and butyrylcholinesterase (AChE/BChE) inhibitors. Compounds 25-31 having a secondary amine moiety connected to the phenyl ring via eight CH2 units spacer were found to be the most potent inhibitors with IC50 value lower than 220 nM and 48 nM against AChE and BChE, respectively. Interestingly, these inhibitors showed a surprising selectively toward BChE, and compounds 26, 27, and 30 displayed 12.5, 18.6, and 18.8-fold higher affinity to BChE. The inhibition kinetics analyzed by Linewear-Burk plots revealed that such compounds were mix-type inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.059
• 作为产物：
  描述：

  二乙胺 、 4-((8-bromooctyl)oxy)benzaldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 以96%的产率得到N-[4-(8-bromooctyloxy)benzyl]-N-ethylethanamine
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Difunctionalized 4-Hydroxybenzaldehyde Derivatives as Novel Cholinesterase Inhibitors

  摘要：

  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。

  DOI：

  10.1248/cpb.58.1216

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。
• Synthesis of 4-[(diethylamino)methyl]-phenol derivatives as novel cholinesterase inhibitors with selectivity towards butyrylcholinesterase
  作者：Liang Yu、Rihui Cao、Wei Yi、Qin Yan、Zhiyong Chen、Lin Ma、Wenlie Peng、Huacan Song

  DOI：10.1016/j.bmcl.2010.04.059

  日期：2010.6

  A series of novel cholinesterase inhibitors, being composed of 4-[(diethylamino) methyl]-phenoxy and secondary amine which were linked with a different length alkyl chain, were designed and synthesized from the starting material p-hydroxybenzaldehyde. These compounds were evaluated as acetylcholinesterase and butyrylcholinesterase (AChE/BChE) inhibitors. Compounds 25-31 having a secondary amine moiety connected to the phenyl ring via eight CH2 units spacer were found to be the most potent inhibitors with IC50 value lower than 220 nM and 48 nM against AChE and BChE, respectively. Interestingly, these inhibitors showed a surprising selectively toward BChE, and compounds 26, 27, and 30 displayed 12.5, 18.6, and 18.8-fold higher affinity to BChE. The inhibition kinetics analyzed by Linewear-Burk plots revealed that such compounds were mix-type inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.