(1E,6E)-1-(3,4-dihydroxyphenyl)-7-(3-cyanophenyl)hepta-1,6-diene-3,5-dione | 1537182-96-9

• 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-(3,4-dihydroxyphenyl)-7-(3-cyanophenyl)hepta-1,6-diene-3,5-dione
• 英文别名: 3-[(1E,6E)-7-(3,4-dihydroxyphenyl)-3,5-dioxohepta-1,6-dienyl]benzonitrile
• CAS: 1537182-96-9
• 化学式: C₂₀H₁₅NO₄
• 分子量: 333.343
• InChiKey: BETQLHPKQHQCDA-NSLJXJERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 boron trioxide 、 硼酸三乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 23.0h， 生成 (1E,6E)-1-(3,4-dihydroxyphenyl)-7-(3-cyanophenyl)hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  Structure activity relationship study of curcumin analogues toward the amyloid-beta aggregation inhibitor

  摘要：

  Inhibition of the amyloid beta aggregation process could possibly prevent the onset of Alzheimer's disease. In this article, we report a structure-activity relationship study of curcumin analogues for anti amyloid beta aggregation activity. Compound 7, the ideal amyloid beta aggregation inhibitor in vitro among synthesized curcumin analogues, has not only potent anti amyloid beta aggregation effects, but also water solubility more than 160 times that of curcumin. In addition, new approaches to improve water solubility of curcumin-type compounds are proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.076

文献信息

• Structure activity relationship study of curcumin analogues toward the amyloid-beta aggregation inhibitor
  作者：Hitoshi Endo、Yuri Nikaido、Mamiko Nakadate、Satomi Ise、Hiroyuki Konno

  DOI：10.1016/j.bmcl.2014.10.076

  日期：2014.12

  Inhibition of the amyloid beta aggregation process could possibly prevent the onset of Alzheimer's disease. In this article, we report a structure-activity relationship study of curcumin analogues for anti amyloid beta aggregation activity. Compound 7, the ideal amyloid beta aggregation inhibitor in vitro among synthesized curcumin analogues, has not only potent anti amyloid beta aggregation effects, but also water solubility more than 160 times that of curcumin. In addition, new approaches to improve water solubility of curcumin-type compounds are proposed. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of curcumin derivatives toward an inhibitor of beta-site amyloid precursor protein cleaving enzyme 1
  作者：Hiroyuki Konno、Hitoshi Endo、Satomi Ise、Keiki Miyazaki、Hideo Aoki、Akira Sanjoh、Kazuya Kobayashi、Yasunao Hattori、Kenichi Akaji

  DOI：10.1016/j.bmcl.2013.11.039

  日期：2014.1

  To research a new non-peptidyl inhibitor of beta-site amyloid precursor protein cleaving enzyme 1, we focused on the curcumin framework, two phenolic groups combined with an sp(2) carbon spacer for low-molecular and high lipophilicity. The structure-activity relationship study of curcumin derivatives is described. Our results indicate that phenolic hydroxy groups and an alkenyl spacer are important structural factors for the inhibition of beta-site amyloid precursor protein cleaving enzyme 1 and, furthermore, non-competitive inhibition of enzyme activity is anticipated from an inhibitory kinetics experiment and docking simulation. (C) 2013 Elsevier Ltd. All rights reserved.