(1E,6E)-1-(benzo[1,3]dioxol-5-yl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (1E,6E)-1-(benzo[1,3]dioxol-5-yl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• 英文别名: (1E,6E)-1-(1,3-benzodioxol-5-yl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• 化学式: C₂₁H₁₈O₆
• 分子量: 366.37
• InChiKey: AEILBXHBRAXAQG-YPCIICBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰丙酮 在 boron trioxide 、 硼酸三丁酯 作用下， 以 乙酸乙酯 为溶剂， 反应 3.08h， 生成 (1E,6E)-1-(benzo[1,3]dioxol-5-yl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  Design and synthesis of curcumin derivatives as tau and amyloid β dual aggregation inhibitors

  摘要：

  Alzheimer's disease (AD) is the most common form of dementia. In an AD patient's brain, senile plaques and neurofibrillary tangles, the abnormal aggregates of amyloid beta (A beta) peptide and tau protein, are observed as the two major hallmarks of this disease. To develop a new drug for treatment of AD, we have designed and synthesized a series of curcumin derivatives and evaluated their inhibitory activities against both tau and Ab aggregation. In this study, we describe the development of the more potent aggregation inhibitor 3-[(1E)-2-(1H-indol-6-yl) ethenyl]-5-[(1E)-2-[ 2-methoxy-4-(2-pyridylmethoxy) phenyl] ethenyl]-1H-pyrazole (compound 4, PE859). This compound has a better pharmacokinetic profile and pharmacological efficacy in vivo than curcumin, making it suitable as a drug for AD. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.08.092

文献信息

• NOVEL CURCUMIN DERIVATIVE
  申请人：Takahashi Takashi

  公开号：US20100048901A1

  公开（公告）日：2010-02-25

  The present invention provides a novel compound that is structurally similar to curcumin and has a suppressive effect on Aβ aggregation, a degradative effect on Aβ aggregates, an inhibitory effect on β-secretase, and a protective effect on neurons. The novel compound is a compound represented by the following general formula (Ia) or a salt thereof: wherein R 1 represents a 4-hydroxy-3-methoxyphenyl group or the like, and R 2 represents a 1H-indol-6-yl group or the like.

  本发明提供了一种新型化合物，其结构类似于姜黄素，并具有抑制Aβ聚集、降解Aβ聚集体、抑制β-分泌酶以及保护神经元的作用。该新型化合物是由以下通式(Ia)或其盐所表示的化合物：其中，R1表示4-羟基-3-甲氧基苯基或类似基团，R2表示1H-吲哚-6-基基或类似基团。
• US8962674B2
  申请人：——

  公开号：US8962674B2

  公开（公告）日：2015-02-24
• Design and synthesis of curcumin derivatives as tau and amyloid β dual aggregation inhibitors
  作者：Michiaki Okuda、Ichiro Hijikuro、Yuki Fujita、Takayuki Teruya、Hirochika Kawakami、Takashi Takahashi、Hachiro Sugimoto

  DOI：10.1016/j.bmcl.2016.08.092

  日期：2016.10

  Alzheimer's disease (AD) is the most common form of dementia. In an AD patient's brain, senile plaques and neurofibrillary tangles, the abnormal aggregates of amyloid beta (A beta) peptide and tau protein, are observed as the two major hallmarks of this disease. To develop a new drug for treatment of AD, we have designed and synthesized a series of curcumin derivatives and evaluated their inhibitory activities against both tau and Ab aggregation. In this study, we describe the development of the more potent aggregation inhibitor 3-[(1E)-2-(1H-indol-6-yl) ethenyl]-5-[(1E)-2-[ 2-methoxy-4-(2-pyridylmethoxy) phenyl] ethenyl]-1H-pyrazole (compound 4, PE859). This compound has a better pharmacokinetic profile and pharmacological efficacy in vivo than curcumin, making it suitable as a drug for AD. (C) 2016 Elsevier Ltd. All rights reserved.