(E)-6-(1H-indol-6-yl)hex-5-ene-2,4-dione

• 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: (E)-6-(1H-indol-6-yl)hex-5-ene-2,4-dione
• 英文别名: 6-(1H-indol-6-yl)hexa-5-ene-2,4-dione；6-(1H-indol-6-yl)hex-5-ene-2,4-dione
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: HFTJIEUJZWVSGY-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-(1H-indol-6-yl)hex-5-ene-2,4-dione 、 2,4-二甲氧基苯甲醛 在 boron trioxide 、 硼酸三异丙酯 、 哌啶 、 盐酸 作用下， 以 乙酸乙酯 、 水 为溶剂， 反应 2.0h， 以87%的产率得到(1E,6E)-1-(2,4-dimethoxyphenyl)-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
• 作为产物：
  描述：

  吲哚-6-甲醛 、 乙酰丙酮 在 boron trioxide 、 盐酸 作用下， 以 水 为溶剂， 生成 (E)-6-(1H-indol-6-yl)hex-5-ene-2,4-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：Sugimoto Hachiro

  公开号：US20110082295A1

  公开（公告）日：2011-04-07

  To develop a highly safe measure to treat Alzheimer's disease using a secretase-inhibiting substance, there is provided a compound represented by the following general formula (I) or a salt thereof: wherein A represents a phenyl group or the like, R 1 represents a chlorine atom, a bromine atom, or a nitro group or the like, R 2 , R 3 , R 4 , and R 5 each represent a hydrogen atom or the like, and L represents CH 2 —CH 2 or CH═CH.

  为了开发一种高度安全的措施来治疗阿尔茨海默病，提供了一种由以下一般式（I）或其盐表示的化合物： 其中A代表苯基或类似物，R1代表氯原子、溴原子或硝基团等，R2、R3、R4和R5各自代表氢原子或类似物，L代表CH2—CH2或CH═CH。
• Novel Pyrazole Derivative
  申请人：Green Tech Co., Ltd.

  公开号：US20150252029A1

  公开（公告）日：2015-09-10

  Provided is a novel therapeutic means for Alzheimer's disease. In particular, provided is a compound represented by the following general formula (I): or a salt thereof.

  提供了一种治疗阿尔茨海默病的新型治疗手段。具体而言，提供了一种由以下通式（I）表示的化合物或其盐。
• Pyrazole derivative
  申请人：GREEN TECH CO., LTD.

  公开号：US09321752B2

  公开（公告）日：2016-04-26

  Provided is a novel therapeutic means for Alzheimer's disease. In particular, provided is a compound represented by the following general formula (I): or a salt thereof.

  提供了一种治疗阿尔茨海默病的新型治疗手段。特别地，提供了一种由以下一般式(I)所代表的化合物或其盐。
• THERAPEUTIC AGENT FOR ALZHEIMER'S DISEASE
  申请人：Tokyo Institute of Technology

  公开号：EP2305629A1

  公开（公告）日：2011-04-06

  To develop a highly safe measure to treat Alzheimer's disease using a secretase-inhibiting substance, there is provided a compound represented by the following general formula (I) or a salt thereof: wherein A represents a phenyl group or the like, R1 represents a chlorine atom, a bromine atom, or a nitro group or the like, R2, R3, R4, and R5 each represent a hydrogen atom or the like, and L represents CH2-CH2 or CH=CH.

  为了开发一种使用分泌酶抑制物质治疗阿尔茨海默病的高度安全的措施，提供了由下式通式（I）代表的化合物或其盐： 其中 A 代表苯基或类似物，R1 代表氯原子、溴原子或硝基或类似物，R2、R3、R4 和 R5 各代表氢原子或类似物，L 代表 CH2-CH2 或 CH=CH。
• NOVEL PYRAZOLE DERIVATIVE
  申请人：Green Tech Co., Ltd.

  公开号：EP2698368B1

  公开（公告）日：2018-02-14