2-(4-(dimethylamino)phenyl)-7-(3-(4-(3-((1,2,3,4-tetrahydroacridin-9-yl)amino)propyl)piperazin-1-yl)propoxy)-4H-chromen-4-one | 1489103-16-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-(dimethylamino)phenyl)-7-(3-(4-(3-((1,2,3,4-tetrahydroacridin-9-yl)amino)propyl)piperazin-1-yl)propoxy)-4H-chromen-4-one
• 英文别名: 2-[4-(Dimethylamino)phenyl]-7-[3-[4-[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]piperazin-1-yl]propoxy]chromen-4-one；2-[4-(dimethylamino)phenyl]-7-[3-[4-[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]piperazin-1-yl]propoxy]chromen-4-one
• CAS: 1489103-16-3
• 化学式: C₄₀H₄₇N₅O₃
• 分子量: 645.845
• InChiKey: HZYJRKKNDYPBCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  9-氯-1,2,3,4-四氢吖啶 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 20.0h， 生成 2-(4-(dimethylamino)phenyl)-7-(3-(4-(3-((1,2,3,4-tetrahydroacridin-9-yl)amino)propyl)piperazin-1-yl)propoxy)-4H-chromen-4-one
  参考文献：
  名称：

  Multifunctional tacrine–flavonoid hybrids with cholinergic, β-amyloid-reducing, and metal chelating properties for the treatment of Alzheimer's disease

  摘要：

  A new series of tacrine flavonoid hybrids (13a u) had been designed, synthesized, and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). In vitro studies showed that most of the molecules exhibited a significant ability to inhibit ChE and self-induced amyloid-beta (A beta(1-42)) aggregation. Kinetic and molecular modeling studies also indicated compounds were mixed-type inhibitors, binding simultaneously to active, peripheral and mid-gorge sites of AChE. Particularly, compound 13k was found to be highly potent and showed a balanced inhibitory profile against ChE and self-induced A beta(1-42) aggregation. Moreover, it also showed excellent metal chelating property and low cell toxicity. These results suggested that 13k might be an excellent multifunctional agent for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.024

文献信息

• Multifunctional tacrine–flavonoid hybrids with cholinergic, β-amyloid-reducing, and metal chelating properties for the treatment of Alzheimer's disease
  作者：Su-Yi Li、Xiao-Bing Wang、Sai-Sai Xie、Neng Jiang、Kelvin D.G. Wang、He-Quan Yao、Hong-Bin Sun、Ling-Yi Kong

  DOI：10.1016/j.ejmech.2013.09.024

  日期：2013.11

  A new series of tacrine flavonoid hybrids (13a u) had been designed, synthesized, and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). In vitro studies showed that most of the molecules exhibited a significant ability to inhibit ChE and self-induced amyloid-beta (A beta(1-42)) aggregation. Kinetic and molecular modeling studies also indicated compounds were mixed-type inhibitors, binding simultaneously to active, peripheral and mid-gorge sites of AChE. Particularly, compound 13k was found to be highly potent and showed a balanced inhibitory profile against ChE and self-induced A beta(1-42) aggregation. Moreover, it also showed excellent metal chelating property and low cell toxicity. These results suggested that 13k might be an excellent multifunctional agent for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.