7-(3-bromopropoxy)-2-(4-(dimethylamino)phenyl)-4H-chromen-4-one | 1489101-89-4

• 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: 7-(3-bromopropoxy)-2-(4-(dimethylamino)phenyl)-4H-chromen-4-one
• CAS: 1489101-89-4
• 化学式: C₂₀H₂₀BrNO₃
• 分子量: 402.288
• InChiKey: JBEOPAOONBVBTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-(3-bromopropoxy)-2-(4-(dimethylamino)phenyl)-4H-chromen-4-one 、 N-(3-(piperazin-1-yl)propyl)-1,2,3,4-tetrahydroacridin-9-amine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以49.5%的产率得到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
• 作为产物：
  描述：

  聚合甲醛 、 2-(4-aminophenyl)-7-(3-bromopropoxy)-4H-chromen-4-one 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 3.0h， 生成 7-(3-bromopropoxy)-2-(4-(dimethylamino)phenyl)-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