2-[3-(7-bromoheptyloxy)phenyl]benzofuran | 1333995-95-1

• 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-[3-(7-bromoheptyloxy)phenyl]benzofuran
• 英文别名: 2-[3-(7-Bromoheptoxy)phenyl]-1-benzofuran
• CAS: 1333995-95-1
• 化学式: C₂₁H₂₃BrO₂
• 分子量: 387.316
• InChiKey: QQVQWDGBGIJBRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[3-(7-bromoheptyloxy)phenyl]benzofuran 在 四氯化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 C₃₇H₃₉NO₃
  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-羟基苄基)三苯基溴化膦 在 三溴化硼 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 生成 2-[3-(7-bromoheptyloxy)phenyl]benzofuran
  参考文献：
  名称：

  Multi-target strategy to address Alzheimer’s disease: Design, synthesis and biological evaluation of new tacrine-based dimers

  摘要：

  The multifactorial nature of Alzheimer's disease (AD) offers us a textbook example where parental compounds, mostly marketed, are modified with the aim of improving and/or conferring two or even more biological activities to contrast or less frequently revert the disease's symptoms. This is the case of tacrine and its dimeric derivative bis(7)-tacrine which, for instance, paved the way for the development of a broad collection of very interesting homo- and heterodimeric structures, conceived in light of the emerging multi-target approach for AD-related drug discovery. As a contribution to the topic, we report here the design, synthesis and biological evaluation of 12 compounds referable to bis(7)-tacrine. In addition to the cholinesterase activity, some of the selected compounds (7-9 and 12) were capable of inhibiting the non-enzymatic function of AChE and/or showed a remarkable activity against BACE1. Thus, the present study outlines a series of newly synthesized molecules, structurally related to bis(7)-tacrine, endowed with extended biological profile in agreement with the emerging multi-target paradigm. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.004