(1E,6E)-1,7-bis(2-hydroxyphenyl)-4, 4-dimethylhepta-1,6-diene-3,5-dione | 1266226-77-0

• 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)-1,7-bis(2-hydroxyphenyl)-4, 4-dimethylhepta-1,6-diene-3,5-dione
• 英文别名: (1E,6E)-1,7-bis(2-hydroxyphenyl)-4,4-dimethylhepta-1,6-diene-3,5-dione
• CAS: 1266226-77-0
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: CIXXXHTXMXXOIK-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (1E,6E)-1,7-bis(2-hydroxyphenyl)-4, 4-dimethylhepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  Design, synthesis, and evaluation of curcumin derivatives as Nrf2 activators and cytoprotectors against oxidative death

  摘要：

  Activation of nuclear factor erythroid-2-related factor 2 (Nrf2) has been proven to be an effective means to prevent the development of cancer, and natural curcumin stands out as a potent Nrf2 activator and cancer chemopreventive agent. In this study, we synthesized a series of curcumin analogs by introducing the geminal dimethyl substituents on the active methylene group to find more potent Nrf2 activators and cytoprotectors against oxidative death. The geminally dimethylated and catechol-type curcumin analog (compound 3) was identified as a promising lead molecule in terms of its increased stability and cytoprotective activity against the tert-butyl hydroperoxide (t-BHP)-induced death of HepG2 cells. Mechanism studies indicate that its cytoprotective effects are mediated by activating the Nrf2 signaling pathway in the Michael acceptor- and catechol-dependent manners. Additionally, we verified by using copper and iron ion chelators that the two metal ion-mediated oxidations of compound 3 to its corresponding electrophilic sigma-quinone, contribute significantly to its Nrf2-dependent cytoprotection. This work provides an example of successfully designing natural curcumin-directed Nrf2 activators by a stability-increasing and proelectrophilic strategy. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.008