(E)-6-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}-2-(3,4,5-trimethoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one | 854716-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (E)-6-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}-2-(3,4,5-trimethoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: (2E)-6-[7-[(3-hydroxyphenyl)methyl-methylamino]heptoxy]-2-[(3,4,5-trimethoxyphenyl)methylidene]-3,4-dihydronaphthalen-1-one
• CAS: 854716-77-1
• 化学式: C₃₅H₄₃NO₆
• 分子量: 573.73
• InChiKey: YLUMANAENFWAME-TURZUDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-6-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}-2-(3,4,5-trimethoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-one 、 异氰酸甲酯 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 3-{[methyl(7-{[(6E)-5-oxo-6-(3,4,5-trimethoxybenzylidene)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}heptyl)amino]methyl}phenyl 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-羟基-1-四氢萘酮 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 20.0h， 生成 (E)-6-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}-2-(3,4,5-trimethoxybenzylidene)-3,4-dihydro-2H-naphthalen-1-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.