6-(7-bromoheptyloxy)benzofuran-3-one | 854716-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 6-(7-bromoheptyloxy)benzofuran-3-one
• 英文别名: 6-(7-Bromoheptoxy)-1-benzofuran-3-one
• CAS: 854716-67-9
• 化学式: C₁₅H₁₉BrO₃
• 分子量: 327.218
• InChiKey: GFUSKSYJSVKDQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  53-54 °C(Solv: toluene (108-88-3))
• 沸点：
  449.8±45.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(7-bromoheptyloxy)benzofuran-3-one 在 aluminum oxide 、 sodium iodide 作用下， 以 二氯甲烷 、 甲苯 、 丁酮 为溶剂， 反应 23.0h， 生成 (Z)-2-benzylidene-6-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}benzofuran-3-one
  参考文献：
  名称：

  Cholinesterase Inhibitors:  Xanthostigmine Derivatives Blocking the Acetylcholinesterase-Induced β-Amyloid Aggregation

  摘要：

  In continuing research that led us to identify a now class of carbamate derivatives acting as potent (Rampa et al. J. Med. Chem. 1998, 41, 3976) and long-lasting (Rampa et al. J. Med. Chem. 2001, 44, 3810) acetylcholinesterase (AChE) inhibitors, we obtained sonic analogues able to simultaneously block both the catalytic and the beta-amyloid (A beta) proaggregatory activities of AChE. The key feature of these derivatives is a 2-arylidenebenzocycloalkanone moiety that provides the ability to bind at the AChE peripheral site responsible for promoting the A beta aggregation. The new carbamates were tested in vitro for the inhibition of both cholinesterases and also for the ability to prevent the AChE-induced All aggregation. All of the compounds had AChE IC50 values in the nanomolar range and showed the ability to block the AChE-induced A beta aggregation, thus supporting the feasibility of this new strategy in the search of compounds for the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm049515h
• 作为产物：
  描述：

  6-羟基-2H-苯并呋喃-3-酮 、 1,7-二溴庚烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以95%的产率得到6-(7-bromoheptyloxy)benzofuran-3-one
  参考文献：
  名称：

  Cholinesterase Inhibitors:  Xanthostigmine Derivatives Blocking the Acetylcholinesterase-Induced β-Amyloid Aggregation

  摘要：

  In continuing research that led us to identify a now class of carbamate derivatives acting as potent (Rampa et al. J. Med. Chem. 1998, 41, 3976) and long-lasting (Rampa et al. J. Med. Chem. 2001, 44, 3810) acetylcholinesterase (AChE) inhibitors, we obtained sonic analogues able to simultaneously block both the catalytic and the beta-amyloid (A beta) proaggregatory activities of AChE. The key feature of these derivatives is a 2-arylidenebenzocycloalkanone moiety that provides the ability to bind at the AChE peripheral site responsible for promoting the A beta aggregation. The new carbamates were tested in vitro for the inhibition of both cholinesterases and also for the ability to prevent the AChE-induced All aggregation. All of the compounds had AChE IC50 values in the nanomolar range and showed the ability to block the AChE-induced A beta aggregation, thus supporting the feasibility of this new strategy in the search of compounds for the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm049515h

文献信息

• Cholinesterase Inhibitors:  Xanthostigmine Derivatives Blocking the Acetylcholinesterase-Induced β-Amyloid Aggregation
  作者：Federica Belluti、Angela Rampa、Lorna Piazzi、Alessandra Bisi、Silvia Gobbi、Manuela Bartolini、Vincenza Andrisano、Andrea Cavalli、Maurizio Recanatini、Piero Valenti

  DOI：10.1021/jm049515h

  日期：2005.6.1

  In continuing research that led us to identify a now class of carbamate derivatives acting as potent (Rampa et al. J. Med. Chem. 1998, 41, 3976) and long-lasting (Rampa et al. J. Med. Chem. 2001, 44, 3810) acetylcholinesterase (AChE) inhibitors, we obtained sonic analogues able to simultaneously block both the catalytic and the beta-amyloid (A beta) proaggregatory activities of AChE. The key feature of these derivatives is a 2-arylidenebenzocycloalkanone moiety that provides the ability to bind at the AChE peripheral site responsible for promoting the A beta aggregation. The new carbamates were tested in vitro for the inhibition of both cholinesterases and also for the ability to prevent the AChE-induced All aggregation. All of the compounds had AChE IC50 values in the nanomolar range and showed the ability to block the AChE-induced A beta aggregation, thus supporting the feasibility of this new strategy in the search of compounds for the treatment of Alzheimer's disease.