(E)-1-(4-amino-2-hydroxyphenyl)-3-(naphthalen-2-yl)-prop-2-en-1-one | 1448349-13-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(4-amino-2-hydroxyphenyl)-3-(naphthalen-2-yl)-prop-2-en-1-one
• 英文别名: (E)-1-(4-amino-2-hydroxyphenyl)-3-naphthalen-2-ylprop-2-en-1-one
• CAS: 1448349-13-0
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: KBVKGJFDVCFBCP-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-amino-2-hydroxyphenyl)-3-(naphthalen-2-yl)-prop-2-en-1-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 3.0h， 以50%的产率得到1-(4-amino-2-hydroxyphenyl)-3-(naphthalen-2-yl)propan-1-one
  参考文献：
  名称：

  Synthesis and Identification of New Flavonoids Targeting Liver X Receptor β Involved Pathway as Potential Facilitators of Aβ Clearance with Reduced Lipid Accumulation

  摘要：

  Alzheimer's disease (AD) is associated with impaired A beta degradation in the brain. Enhancing the process of A beta clearance is an attractive potential AD therapy. Treatment with LXR agonists may reduce A beta levels in vivo. However, the clinical potential of many LXR agonists is limited because of their nonselective actions on LXR alpha/beta, which lead to undesired hepatic lipogenesis via LXR alpha-dependent pathways. In this study, ABCA1 up-regulators were identified from a series of flavonoids and were found to preferentially activate LXR beta and up-regulate expression of ABCA1 and apoE in different cell lines. Further investigations confirmed that these compounds facilitate intracellular A beta clearance in A beta-loaded BV2 cells. Administration of compound 19 reduced total brain A beta and plaque burden in APP/PS1 double transgenic mice, associated with elevated ABCA1 and apoE expression. Compared with the nonselective LXR agonists, the active compounds reported here induced less accumulation of undesired lipids and triglycerides in HepG2 cells.

  DOI：

  10.1021/jm301913k
• 作为产物：
  描述：

  二乙酰基-3-氨基苯酚 在 盐酸 、 aluminum (III) chloride 、 lithium hydrochloride monohydrate 作用下， 以 乙醇 、 水 为溶剂， 反应 8.67h， 生成 (E)-1-(4-amino-2-hydroxyphenyl)-3-(naphthalen-2-yl)-prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and Identification of New Flavonoids Targeting Liver X Receptor β Involved Pathway as Potential Facilitators of Aβ Clearance with Reduced Lipid Accumulation

  摘要：

  Alzheimer's disease (AD) is associated with impaired A beta degradation in the brain. Enhancing the process of A beta clearance is an attractive potential AD therapy. Treatment with LXR agonists may reduce A beta levels in vivo. However, the clinical potential of many LXR agonists is limited because of their nonselective actions on LXR alpha/beta, which lead to undesired hepatic lipogenesis via LXR alpha-dependent pathways. In this study, ABCA1 up-regulators were identified from a series of flavonoids and were found to preferentially activate LXR beta and up-regulate expression of ABCA1 and apoE in different cell lines. Further investigations confirmed that these compounds facilitate intracellular A beta clearance in A beta-loaded BV2 cells. Administration of compound 19 reduced total brain A beta and plaque burden in APP/PS1 double transgenic mice, associated with elevated ABCA1 and apoE expression. Compared with the nonselective LXR agonists, the active compounds reported here induced less accumulation of undesired lipids and triglycerides in HepG2 cells.

  DOI：

  10.1021/jm301913k

文献信息

• Synthesis and Identification of New Flavonoids Targeting Liver X Receptor β Involved Pathway as Potential Facilitators of Aβ Clearance with Reduced Lipid Accumulation
  作者：Yun Hu、Yaqi Yang、Yanjun Yu、Gesi Wen、Nana Shang、Wei Zhuang、Dihan Lu、Binhua Zhou、Baoxia Liang、Xin Yue、Feng Li、Jun Du、Xianzhang Bu

  DOI：10.1021/jm301913k

  日期：2013.8.8

  Alzheimer's disease (AD) is associated with impaired A beta degradation in the brain. Enhancing the process of A beta clearance is an attractive potential AD therapy. Treatment with LXR agonists may reduce A beta levels in vivo. However, the clinical potential of many LXR agonists is limited because of their nonselective actions on LXR alpha/beta, which lead to undesired hepatic lipogenesis via LXR alpha-dependent pathways. In this study, ABCA1 up-regulators were identified from a series of flavonoids and were found to preferentially activate LXR beta and up-regulate expression of ABCA1 and apoE in different cell lines. Further investigations confirmed that these compounds facilitate intracellular A beta clearance in A beta-loaded BV2 cells. Administration of compound 19 reduced total brain A beta and plaque burden in APP/PS1 double transgenic mice, associated with elevated ABCA1 and apoE expression. Compared with the nonselective LXR agonists, the active compounds reported here induced less accumulation of undesired lipids and triglycerides in HepG2 cells.