2-丙烯-1-酮,1-(2,6-二羟基苯基)-3-(4-甲氧苯基)- | 108896-92-0

• 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
• 中文名称: 2-丙烯-1-酮,1-(2,6-二羟基苯基)-3-(4-甲氧苯基)-
• 英文名称: 2′,6′-dihydroxy-4-methoxychalcone
• 英文别名: 1-(2,6-Dihydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 108896-92-0
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: LUKXMYDKUCDMRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-丙烯-1-酮,1-(2,6-二羟基苯基)-3-(4-甲氧苯基)- 在 palladium on activated charcoal 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 5-Hydroxy-3-[(4-methoxyphenyl)methyl]chromen-4-one
  参考文献：
  名称：

  New homoisoflavonoid analogues protect cells by regulating autophagy

  摘要：

  As a special group of naturally occurring flavonoids, homoisoflavonoids have been discovered as active components of several traditional Chinese medicines for nourishing heart and mind. In this study, twenty homoisoflavonoid analogues, including different substitution groups on rings A and B, as well as heteroaromatic B ring, were synthesized and evaluated for their cardioprotective and neuroprotective activities. In a H2O2-induced H9c2 cardiomyocytes injury assay, nine homoisoflavonoid analogues showed promising activities in the same level as the positive control, diazoxide. Six cardioprotective compounds with representative structure diversities were then evaluated for their neuroprotective effects on MPP+ induced SH-SY5Y cell injury model. Furthermore, autophagy inducing monodansylcadaverine (MDC) fluorescence staining methods and molecular docking studies indicated the action mechanism of these compounds may involve autophagy regulating via class I P13K signaling pathway. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.01.086
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-丙烯-1-酮,1-(2,6-二羟基苯基)-3-(4-甲氧苯基)-
  参考文献：
  名称：

  New homoisoflavonoid analogues protect cells by regulating autophagy

  摘要：

  As a special group of naturally occurring flavonoids, homoisoflavonoids have been discovered as active components of several traditional Chinese medicines for nourishing heart and mind. In this study, twenty homoisoflavonoid analogues, including different substitution groups on rings A and B, as well as heteroaromatic B ring, were synthesized and evaluated for their cardioprotective and neuroprotective activities. In a H2O2-induced H9c2 cardiomyocytes injury assay, nine homoisoflavonoid analogues showed promising activities in the same level as the positive control, diazoxide. Six cardioprotective compounds with representative structure diversities were then evaluated for their neuroprotective effects on MPP+ induced SH-SY5Y cell injury model. Furthermore, autophagy inducing monodansylcadaverine (MDC) fluorescence staining methods and molecular docking studies indicated the action mechanism of these compounds may involve autophagy regulating via class I P13K signaling pathway. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.01.086

文献信息

• Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists
  作者：Guoning Zhang、Shuainan Liu、Wenjuan Tan、Ruchi Verma、Yuan Chen、Deyang Sun、Yi Huan、Qian Jiang、Xing Wang、Na Wang、Yang Xu、Chiwai Wong、Zhufang Shen、Ruitang Deng、Jinsong Liu、Yanqiao Zhang、Weishuo Fang

  DOI：10.1016/j.ejmech.2017.02.037

  日期：2017.3

  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.