1-(4-hydroxyphenyl)-7-(2-hydroxy-3,4-dimethoxyphenyl)heptan-3-ol | 68486-80-6

• 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: 1-(4-hydroxyphenyl)-7-(2-hydroxy-3,4-dimethoxyphenyl)heptan-3-ol
• 英文别名: 6-(5-hydroxy-7-(4-hydroxyphenyl)heptyl)-2,3-dimethoxyphenol
• CAS: 68486-80-6
• 化学式: C₂₁H₂₈O₅
• 分子量: 360.45
• InChiKey: FOMUTLZQHOHPMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(4-hydroxyphenyl)-7-(2-hydroxy-3,4-dimethoxyphenyl)heptan-3-ol 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以95%的产率得到1-(4-hydroxyphenyl)-7-(5-bromo-2-hydroxy-3,4-dimethoxyphenyl)heptan-3-ol
  参考文献：
  名称：

  Whiting, Donald A.; Wood, Andrew F., Journal of the Chemical Society. Perkin transactions I, 1980, p. 623 - 628

  摘要：

  DOI：
• 作为产物：
  描述：

  6-allyl-2,3-dimethoxyphenol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-(4-hydroxyphenyl)-7-(2-hydroxy-3,4-dimethoxyphenyl)heptan-3-ol
  参考文献：
  名称：

  聚合全合成（±）肉豆蔻醇，一种环状天然二芳基庚烷

  摘要：

  据报道，杨梅醇的一种成分杨梅醇1可以降低微管相关蛋白tau（MAPT）的水平，该蛋白tau的积累在某些神经退行性疾病（例如阿尔茨海默氏病（AD））中起着重要作用。本文中，我们描述了一种新的合成路线，该路线可从9步制备丁香油，总收率为4.9％，从商业上可获得的2,3-二甲氧基苯酚和3-（4-苄氧基苯基）丙酸甲酯开始。关键步骤是交叉复分解以获得线性二芳基庚烷中间体和Suzuki-Miyaura多米诺反应以生成具有挑战性的大环。

  DOI：

  10.1039/c8ob02052c

文献信息

• Henley-Smith, Peter; Whiting, Donald A.; Wood, Andrew F., Journal of the Chemical Society. Perkin transactions I, 1980, p. 614 - 622
  作者：Henley-Smith, Peter、Whiting, Donald A.、Wood, Andrew F.

  DOI：——

  日期：——
• New synthesized polyoxygenated diarylheptanoids suppress lipopolysaccharide-induced neuroinflammation
  作者：Anna Santarsiero、Antonella Bochicchio、Maria Funicello、Paolo Lupattelli、Sabine Choppin、Françoise Colobert、Gilles Hanquet、Lucie Schiavo、Paolo Convertini、Lucia Chiummiento、Vittoria Infantino

  DOI：10.1016/j.bbrc.2020.06.122

  日期：2020.9

  In neurodegenerative diseases, such as Alzheimer's disease, Huntington's disease, Parkinson's disease and multiple sclerosis, neuroinflammation induced by the microglial activation plays a crucial role. In effort to develop effective anti-neuroinflammatory compounds, different new linear polyoxygenated diarylheptanoids were synthesized. In LPS-triggered BV-2 microglial cells their ability to reduce the concentration of IL-6 and TNF-alpha pro-inflammatory cytokines was evaluated. Moreover, their effect on NF-kappa B and ATP citrate lyase (ACLY), a recently emerged target of metabolic reprogramming in inflammation, was assessed. Finally, we turned our attention to inflammatory mediators derived from the cleavage of citrate catalyzed by ACLY: prostaglandin E-2, nitric oxide and reactive oxygen species. All compounds showed null or minimal cytotoxicity; most of them had a great anti-neuroinflammatory activity. Diarylheptanoids 6b and 6c, bearing a halide atom and benzyl ether protective groups, exhibited the best effect since they blocked the secretion of all inflammatory mediators analyzed and reduced NF-kB and ACLY protein levels. (c) 2020 Elsevier Inc. All rights reserved.