(E)-5-(4-Bromobut-2-enyloxy)-1-hydroxy-3,6-bis(2-methylbut-3-en-2-yloxy)-9H-xanthen-9-one | 1383484-74-9

• 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: (E)-5-(4-Bromobut-2-enyloxy)-1-hydroxy-3,6-bis(2-methylbut-3-en-2-yloxy)-9H-xanthen-9-one
• 英文别名: 5-[(E)-4-bromobut-2-enoxy]-1-hydroxy-3,6-bis(2-methylbut-3-en-2-yloxy)xanthen-9-one
• CAS: 1383484-74-9
• 化学式: C₂₇H₂₉BrO₆
• 分子量: 529.428
• InChiKey: QDTOBFFFUKISEQ-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯乙酸 、 (E)-5-(4-Bromobut-2-enyloxy)-1-hydroxy-3,6-bis(2-methylbut-3-en-2-yloxy)-9H-xanthen-9-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 [(E)-4-[8-hydroxy-3,6-bis(2-methylbut-3-en-2-yloxy)-9-oxoxanthen-4-yl]oxybut-2-enyl] 2-phenylacetate
  参考文献：
  名称：

  Garcinia Xanthones as Orally Active Antitumor Agents

  摘要：

  Using a newly developed strategy whose key step is the regioselective propargylation of hydroxyxanthone substrates, 99 structurally diverse Garcinia natural-product-like xanthones based on gambogic acid were designed and synthesized and their in vitro antitumor activity was evaluated. A set of 40 related compounds was chosen for determination of their physicochemical properties including polar surface area, log D-7.4, aqueous solubility, and permeability at pH 7.4. In the light of the in vitro antitumor activity and the physicochemical properties, two compounds were advanced into in vivo efficacy experiments. The antitumor activity of compound 112, administered po, showed more potent in vivo oral antitumor activity than gambogic acid.

  DOI：

  10.1021/jm301593r
• 作为产物：
  描述：

  1,3,5,6-四羟基呫吨酮 在 copper(l) iodide 、 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 丙酮 、 乙腈 为溶剂， 25.0~50.0 ℃ 、101.33 kPa 条件下， 反应 6.67h， 生成 (E)-5-(4-Bromobut-2-enyloxy)-1-hydroxy-3,6-bis(2-methylbut-3-en-2-yloxy)-9H-xanthen-9-one
  参考文献：
  名称：

  Garcinia Xanthones as Orally Active Antitumor Agents

  摘要：

  Using a newly developed strategy whose key step is the regioselective propargylation of hydroxyxanthone substrates, 99 structurally diverse Garcinia natural-product-like xanthones based on gambogic acid were designed and synthesized and their in vitro antitumor activity was evaluated. A set of 40 related compounds was chosen for determination of their physicochemical properties including polar surface area, log D-7.4, aqueous solubility, and permeability at pH 7.4. In the light of the in vitro antitumor activity and the physicochemical properties, two compounds were advanced into in vivo efficacy experiments. The antitumor activity of compound 112, administered po, showed more potent in vivo oral antitumor activity than gambogic acid.

  DOI：

  10.1021/jm301593r