8-hydroxy-2-(4-methoxy-phenyl)-chromen-4-one | 743438-43-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 8-hydroxy-2-(4-methoxy-phenyl)-chromen-4-one
• 英文别名: 8-Hydroxy-2-(4-methoxy-phenyl)-chromen-4-on；8-Hydroxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 743438-43-9
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: FPMCTVGSXLDOSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-hydroxy-2-(4-methoxy-phenyl)-chromen-4-one 生成 8-acetoxy-2-(4-methoxy-phenyl)-chromen-4-one
  参考文献：
  名称：

  Baker et al., Journal of the Chemical Society, 1949, p. 1560

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二羟基苯乙酮 在 碘 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.83h， 生成 8-hydroxy-2-(4-methoxy-phenyl)-chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

  摘要：

  Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.037