7-((6-bromohexyl)oxy)-4-methoxy-2H-chromen-2-one | 1444415-86-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-((6-bromohexyl)oxy)-4-methoxy-2H-chromen-2-one
• 英文别名: 7-(6-Bromohexoxy)-4-methoxychromen-2-one；7-(6-bromohexoxy)-4-methoxychromen-2-one
• CAS: 1444415-86-4
• 化学式: C₁₆H₁₉BrO₄
• 分子量: 355.228
• InChiKey: WGRFRFHHWSPKPS-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C
• 沸点：
  503.9±50.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(piperazin-1-yl)-N-(1,2,3,4-tetrahydro-acridin-9-yl)acetamide 、 7-((6-bromohexyl)oxy)-4-methoxy-2H-chromen-2-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以41%的产率得到2-(4-(6-((4-methoxy-2-oxo-2H-chromen-7-yl)oxy)hexyl)piperazin-1-yl)-N-(1,2,3,4-tetrahydroacridin-9-yl)acetamide
  参考文献：
  名称：

  Design, synthesis and evaluation of novel tacrine–coumarin hybrids as multifunctional cholinesterase inhibitors against Alzheimer's disease

  摘要：

  A series of tacrine-coumarin hybrids (8a-t) were designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit ChE and self-induced,beta-amyloid (A beta) aggregation, and to act as metal chelators. Especially, 8f displayed the greatest ability to inhibit acetylcholinesterase (AChE, IC50 = 0.092 mu M) and A beta aggregation (67.8%, 20 mu M). It was also a good butyrylcholinesterase inhibitor (BuChE, IC50 = 0.234 mu M) and metal chelator. Besides, kinetic and molecular modeling studies indicated that 8f was a mixed-type inhibitor, binding simultaneously to active, peripheral and mid-gorge sites of AChE. These results suggested that 8f might be an excellent multifunctional agent for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.051
• 作为产物：
  描述：

  4,7-二羟基香豆素 在 盐酸 、 水 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.5h， 生成 7-((6-bromohexyl)oxy)-4-methoxy-2H-chromen-2-one
  参考文献：
  名称：

  Design, synthesis and evaluation of novel tacrine–coumarin hybrids as multifunctional cholinesterase inhibitors against Alzheimer's disease

  摘要：

  A series of tacrine-coumarin hybrids (8a-t) were designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit ChE and self-induced,beta-amyloid (A beta) aggregation, and to act as metal chelators. Especially, 8f displayed the greatest ability to inhibit acetylcholinesterase (AChE, IC50 = 0.092 mu M) and A beta aggregation (67.8%, 20 mu M). It was also a good butyrylcholinesterase inhibitor (BuChE, IC50 = 0.234 mu M) and metal chelator. Besides, kinetic and molecular modeling studies indicated that 8f was a mixed-type inhibitor, binding simultaneously to active, peripheral and mid-gorge sites of AChE. These results suggested that 8f might be an excellent multifunctional agent for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.051

文献信息

• Design, synthesis and evaluation of novel tacrine–coumarin hybrids as multifunctional cholinesterase inhibitors against Alzheimer's disease
  作者：Sai-Sai Xie、Xiao-Bing Wang、Jiang-Yan Li、Lei Yang、Ling-Yi Kong

  DOI：10.1016/j.ejmech.2013.03.051

  日期：2013.6

  A series of tacrine-coumarin hybrids (8a-t) were designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit ChE and self-induced,beta-amyloid (A beta) aggregation, and to act as metal chelators. Especially, 8f displayed the greatest ability to inhibit acetylcholinesterase (AChE, IC50 = 0.092 mu M) and A beta aggregation (67.8%, 20 mu M). It was also a good butyrylcholinesterase inhibitor (BuChE, IC50 = 0.234 mu M) and metal chelator. Besides, kinetic and molecular modeling studies indicated that 8f was a mixed-type inhibitor, binding simultaneously to active, peripheral and mid-gorge sites of AChE. These results suggested that 8f might be an excellent multifunctional agent for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.