(E)-5-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}-2-(3,4,5-trimethoxybenzylidene)-indan-1-one | 854716-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (E)-5-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}-2-(3,4,5-trimethoxybenzylidene)-indan-1-one
• 英文别名: (2E)-5-[7-[(3-hydroxyphenyl)methyl-methylamino]heptoxy]-2-[(3,4,5-trimethoxyphenyl)methylidene]-3H-inden-1-one
• CAS: 854716-75-9
• 化学式: C₃₄H₄₁NO₆
• 分子量: 559.703
• InChiKey: FYJSRENOZKGCEH-WPWMEQJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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)-5-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}-2-(3,4,5-trimethoxybenzylidene)-indan-1-one 、 异氰酸甲酯 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以27%的产率得到3-{[methyl(7-{[(2E)-1-oxo-2-(3,4,5-trimethoxybenzylidene)-2,3-dihydro-1H-inden-5-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：

  1,7-二溴庚烷 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 反应 23.0h， 生成 (E)-5-{7-[(3-hydroxybenzyl)-methylamino]heptyloxy}-2-(3,4,5-trimethoxybenzylidene)-indan-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.