1-Hydroxy-6-methoxyphenanthrene-9,10-dione | 1424243-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-Hydroxy-6-methoxyphenanthrene-9,10-dione
• 英文别名: 1-hydroxy-6-methoxyphenanthrene-9,10-dione
• CAS: 1424243-58-2
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: UKBBICRZQBMANB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  草酰氯 、 3,3-二甲氧基联苯 在 aluminum (III) chloride 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以20%的产率得到1,6-Dimethoxyphenanthrene-9,10-dione
  参考文献：
  名称：

  Synthesis of novel inhibitors blocking Wnt signaling downstream of β-Catenin

  摘要：

  Large scale screening of libraries consisting of natural and small molecules led to the identification of many small molecule inhibitors repressing Wnt/β‐Catenin signaling. However, targeted synthesis of novel Wnt pathway inhibitors has been rarely described. We developed a modular and expedient way to create the aromatic ring system with an aliphatic ring in between. Our synthesis opens up the possibility, in principle, to substitute all positions at the ring system with any desired substituent. Here, we tested five different haloquinone analogs carrying methoxy‐ and hydroxy‐groups at different positions. Bona fide Wnt activity assays in cell culture and in Xenopus embryos revealed that two of these compounds act as potent inhibitors of aberrant activated Wnt/β‐Catenin signaling.

  DOI：

  10.1016/j.febslet.2013.01.034

文献信息

• Synthesis of novel inhibitors blocking Wnt signaling downstream of β-Catenin
  作者：Sonja Halbedl、Marie-Claire Kratzer、Karolin Rahm、Nicoletta Crosta、Kye-Simeon Masters、Jessica Zippert、Stefan Bräse、Dietmar Gradl

  DOI：10.1016/j.febslet.2013.01.034

  日期：2013.3.1

  Large scale screening of libraries consisting of natural and small molecules led to the identification of many small molecule inhibitors repressing Wnt/β‐Catenin signaling. However, targeted synthesis of novel Wnt pathway inhibitors has been rarely described. We developed a modular and expedient way to create the aromatic ring system with an aliphatic ring in between. Our synthesis opens up the possibility, in principle, to substitute all positions at the ring system with any desired substituent. Here, we tested five different haloquinone analogs carrying methoxy‐ and hydroxy‐groups at different positions. Bona fide Wnt activity assays in cell culture and in Xenopus embryos revealed that two of these compounds act as potent inhibitors of aberrant activated Wnt/β‐Catenin signaling.