(Z)-2-(3,4-dichlorobenzylidene)-6-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}benzofuran-3-one | 854717-04-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-2-(3,4-dichlorobenzylidene)-6-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}benzofuran-3-one
• 英文别名: (2Z)-2-[(3,4-dichlorophenyl)methylidene]-6-[7-[(3-hydroxyphenyl)methyl-methylamino]heptoxy]-1-benzofuran-3-one
• CAS: 854717-04-7
• 化学式: C₃₀H₃₁Cl₂NO₄
• 分子量: 540.486
• InChiKey: LLZHNSAREADBNS-MIXAMLLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-2-(3,4-dichlorobenzylidene)-6-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}benzofuran-3-one 、 异氰酸甲酯 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以25%的产率得到3-{[(7-{[(2Z)-2-[(3,4-dichlorophenyl)methylidene]-3-oxo-2,3-dihydro-1-benzofuran-6-yl]oxy}heptyl)(methyl)amino]methyl}phenyl N-methylcarbamate
  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-(7-iodoheptyloxy)benzofuran-3-one 在 aluminum oxide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 (Z)-2-(3,4-dichlorobenzylidene)-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