2,5-二羟基呫吨酮 | 35040-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 2,5-二羟基呫吨酮
• 英文名称: 2,5-dihydroxy-9H-xanthen-9-one
• 英文别名: 4,7(2,5)-Dihydroxyxanthon；2,5-dihydroxyxanthone；2,5-dihydroxy-xanthen-9-one；2,5-Dihydroxyxanthon；2,5-dihydroxyxanthen-9-one
• CAS: 35040-32-5
• 化学式: C₁₃H₈O₄
• 分子量: 228.204
• InChiKey: LXSIVSWCSPREMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  室温

反应信息

• 作为产物：
  描述：

  2,5-dimethoxy-9H-xanthen-9-one 在 三氯化铝 作用下， 以 xylene 为溶剂， 反应 1.0h， 以66.7%的产率得到2,5-二羟基呫吨酮
  参考文献：
  名称：

  Quantitative Struktur-Wirkungs-Beziehung bei Polyhydroxyxanthonen, 2. Mitt.1): Synthese mehrfach oxigenierter 2-Hydroxyxanthone

  摘要：

  Es wird die Synthese der 2-Hydroxyxanthone 8 über die entsprechenden Polymethoxyxanthone 7 beschrieben, die in Ring C mehrfachhydroxyliert sind。Die Darstellung verläuft entweder über die 2-Phenoxybenzosäuren 5 or die polymethoxylierten 2-Hydroxybenzophenone 6。

  DOI：

  10.1002/ardp.19903230307

文献信息

• Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them
  作者：Jie Liu、Jianrun Zhang、Huailing Wang、Zhijun Liu、Cao Zhang、Zhenlei Jiang、Heru Chen

  DOI：10.1016/j.ejmech.2017.03.068

  日期：2017.6

  34 Xanthones were synthesized by microwave assisted technique. Their in vitro inhibition activities against five cell lines growth were evaluated. The SAR has been thoroughly discussed. 7-Bromo-1,3-dihydroxy-9H-xanthen-9-one (3-1) was confirmed as the most active agent against MDA-MB-231 cell line growth with an IC50 of 0.46 +/- 0.03 mu M. Combination of 3-1 and 5,6-dimethylxanthone-4-acetic acid (DMXAA) showed the best synergistic effect. Apoptosis analysis indicated different contributions of early/late apoptosis and necrosis to cell death for both monomers and the combination. Western Blot implied that the combination regulated p53/MDM2 to a better healthy state. Furthermore, 3-1 and DMXAA arrested more cells on G2/M phase; while the combination arrested more cells on S phase. All the evidences support that the 3-1/DMXAA combination is a better anti-cancer therapy. (C) 2017 Elsevier Masson SAS. All rights reserved.