(1E,6E)-1-(4-benzyloxy-2-methoxyphenyl)-7-(1H-indol-6-yl)hepta-1,6-diene-3,5-dione | 1402729-33-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,6E)-1-(4-benzyloxy-2-methoxyphenyl)-7-(1H-indol-6-yl)hepta-1,6-diene-3,5-dione
• 英文别名: (1E,6E)-1-(1H-Indol-6-yl)-7-[2-methoxy-4-(phenylmethoxy)phenyl]-1,6-heptadiene-3,5-dione；(1E,6E)-1-(1H-indol-6-yl)-7-(2-methoxy-4-phenylmethoxyphenyl)hepta-1,6-diene-3,5-dione
• CAS: 1402729-33-2
• 化学式: C₂₉H₂₅NO₄
• 分子量: 451.522
• InChiKey: ZAPPNMGPHQBOBC-SDCOAONHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吲哚-6-甲醛 在 boron trioxide 、 硼酸三异丙酯 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (1E,6E)-1-(4-benzyloxy-2-methoxyphenyl)-7-(1H-indol-6-yl)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

• 1,7-DIARYL-1,6-HEPTADIEN-3,5-DION-DERIVATE, VERFAHREN ZUR HERSTELLUNG UND VERWENDUNG DERSELBEN
  申请人：Universitätsklinikum Regensburg

  公开号：EP3135110A1

  公开（公告）日：2017-03-01

  Die vorliegende Erfindung betrifft 1,7-Diaryl-1,6-heptadien-3,5-dion-Derivate, deren Herstellung und Verwendung.

  本发明涉及 1,7-二基-1,6-庚二烯-3,5-二酮衍生物及其制备和使用。
• NOVEL PYRAZOLE DERIVATIVE
  申请人：Green Tech Co., Ltd.

  公开号：EP2698368B1

  公开（公告）日：2018-02-14
• US9399635B2
  申请人：——

  公开号：US9399635B2

  公开（公告）日：2016-07-26
• 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.