3,5-bis((E)-2,3,4-trimethoxybenzylidene)-1-methylpiperidin-4-one | 1049971-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis((E)-2,3,4-trimethoxybenzylidene)-1-methylpiperidin-4-one
• 英文别名: (3E,5E)-1-methyl-3,5-bis[(2,3,4-trimethoxyphenyl)methylidene]piperidin-4-one
• CAS: 1049971-16-5
• 化学式: C₂₆H₃₁NO₇
• 分子量: 469.535
• InChiKey: QIJNPXNDNGLJPA-KLCVKJMQSA-N

物化性质

• 沸点：
  638.4±55.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 2,3,4-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 水 为溶剂， 以95%的产率得到3,5-bis((E)-2,3,4-trimethoxybenzylidene)-1-methylpiperidin-4-one
  参考文献：
  名称：

  Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin

  摘要：

  Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability, to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues. (C) 2017 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2017.11.048