[2-(4-{7-[(3-hydroxybenzyl)-N-methylamino]heptyloxy}phenyl)benzofuran-3-yl]-p-tolylmethanone | 1416452-99-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: [2-(4-{7-[(3-hydroxybenzyl)-N-methylamino]heptyloxy}phenyl)benzofuran-3-yl]-p-tolylmethanone
• 英文别名: [2-[4-[7-[(3-Hydroxyphenyl)methyl-methylamino]heptoxy]phenyl]-1-benzofuran-3-yl]-(4-methylphenyl)methanone；[2-[4-[7-[(3-hydroxyphenyl)methyl-methylamino]heptoxy]phenyl]-1-benzofuran-3-yl]-(4-methylphenyl)methanone
• CAS: 1416452-99-7
• 化学式: C₃₇H₃₉NO₄
• 分子量: 561.721
• InChiKey: YARBOSILFOTPMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-(4-{7-[(3-hydroxybenzyl)-N-methylamino]heptyloxy}phenyl)benzofuran-3-yl]-p-tolylmethanone 、 异氰酸甲酯 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以54%的产率得到[3-[[methyl-[7-[4-[3-(4-methylbenzoyl)-1-benzofuran-2-yl]phenoxy]heptyl]amino]methyl]phenyl] N-methylcarbamate
  参考文献：
  名称：

  2-Arylbenzofuran-based molecules as multipotent Alzheimer's disease modifying agents

  摘要：

  The complex etiology of Alzheimer's disease prompts scientists to develop multi-target strategies to combat causes and symptoms. In line with this modern paradigm and as a follow-up to our previous studies, we designed and synthesized a focused collection of new 2-arylbenzofurans and evaluated their biological properties towards specific targets involved in AD, namely human AChE and human BuChE, and A beta fibril formation. Selected compounds were also tested for their ability to inhibit A beta neurotoxicity in terms of neuronal viability loss, and to prevent A beta peptide-binding to cell membrane and intracellular reactive oxygen species (ROS) formation. The different modifications introduced in the structure of our lead compound led to an increase in activity towards one or more of the selected targets: the anticholinesterase activity of some compounds was found to be significantly higher than previously obtained related molecules, and the compounds also proved to possess A beta anti-aggregating properties and neuroprotective effects. The most interesting multi-target compounds were 18, and 1. Interestingly, 1 also showed good selectivity and moderate affinity for CB1 receptor, opening new perspectives in the field of research on AD, since cannabinoid ligands have been widely reported to have neuroprotective properties. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.045
• 作为产物：
  描述：

  2-[4-(7-溴庚氧基)苯基]苯并呋喃 在 四氯化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 [2-(4-{7-[(3-hydroxybenzyl)-N-methylamino]heptyloxy}phenyl)benzofuran-3-yl]-p-tolylmethanone
  参考文献：
  名称：

  2-Arylbenzofuran-based molecules as multipotent Alzheimer's disease modifying agents

  摘要：

  The complex etiology of Alzheimer's disease prompts scientists to develop multi-target strategies to combat causes and symptoms. In line with this modern paradigm and as a follow-up to our previous studies, we designed and synthesized a focused collection of new 2-arylbenzofurans and evaluated their biological properties towards specific targets involved in AD, namely human AChE and human BuChE, and A beta fibril formation. Selected compounds were also tested for their ability to inhibit A beta neurotoxicity in terms of neuronal viability loss, and to prevent A beta peptide-binding to cell membrane and intracellular reactive oxygen species (ROS) formation. The different modifications introduced in the structure of our lead compound led to an increase in activity towards one or more of the selected targets: the anticholinesterase activity of some compounds was found to be significantly higher than previously obtained related molecules, and the compounds also proved to possess A beta anti-aggregating properties and neuroprotective effects. The most interesting multi-target compounds were 18, and 1. Interestingly, 1 also showed good selectivity and moderate affinity for CB1 receptor, opening new perspectives in the field of research on AD, since cannabinoid ligands have been widely reported to have neuroprotective properties. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.045