8-hydroxy-1,3-dimethoxy-9H-xanthen-9-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-hydroxy-1,3-dimethoxy-9H-xanthen-9-one
• 英文别名: 8-Hydroxy-1,3-dimethoxyxanthen-9-one；8-hydroxy-1,3-dimethoxyxanthen-9-one
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: NWYOQAWZOQFSBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-二甲氧基苯酚 、 2,6-二羟基苯甲酸 在 zinc(II) chloride 、 三氯氧磷 作用下， 反应 0.5h， 以73.1%的产率得到8-hydroxy-1,3-dimethoxy-9H-xanthen-9-one
  参考文献：
  名称：

  Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2017.03.068

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.