1-hydroxy-3-(2-hydroxy-3-(3-hydroxypropylthio)propoxy)-9H-xanthen-9-one | 1310077-59-8

• 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: 1-hydroxy-3-(2-hydroxy-3-(3-hydroxypropylthio)propoxy)-9H-xanthen-9-one
• 英文别名: 1-Hydroxy-3-[2-hydroxy-3-(3-hydroxypropylsulfanyl)propoxy]xanthen-9-one
• CAS: 1310077-59-8
• 化学式: C₁₉H₂₀O₆S
• 分子量: 376.43
• InChiKey: DCLHYSSWACXVJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,3-二羟基氧杂蒽-9-酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 1-hydroxy-3-(2-hydroxy-3-(3-hydroxypropylthio)propoxy)-9H-xanthen-9-one
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking study of 3-(3′-heteroatom substituted-2′-hydroxy-1′-propyloxy) xanthone analogues as novel topoisomerase IIα catalytic inhibitor

  摘要：

  Epoxide ring-opened xanthone derivatives were synthesized and tested for their topoisomerase inhibitory activity and cytotoxicity. Most of the compounds showed topo II alpha specific inhibitory activity. To clarify the mechanism of action of these compounds, the most potent compound (compound 14) of the synthesized analogues was further studied by testing its ATPase inhibitory activity and through molecular docking experiments. The results showed that the topo II alpha inhibitory activity of compound 14 was inversely proportional to ATP concentration. In the ATPase inhibitory test, ATP hydrolysis was reduced less efficiently by compound 14 (28.5 +/- 4.6%) than novobiocin (60.4 +/- 8.1%). Molecular docking study revealed compound 14 to have a stable binding pattern to the ATP-binding domain of human topo II. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.011

文献信息

• Synthesis, biological evaluation, and molecular docking study of 3-(3′-heteroatom substituted-2′-hydroxy-1′-propyloxy) xanthone analogues as novel topoisomerase IIα catalytic inhibitor
  作者：Kyu-Yeon Jun、Eun-Young Lee、Mi-Ja Jung、Ok-Hee Lee、Eung-Seok Lee、Hea-Young Park Choo、Younghwa Na、Youngjoo Kwon

  DOI：10.1016/j.ejmech.2011.01.011

  日期：2011.6

  Epoxide ring-opened xanthone derivatives were synthesized and tested for their topoisomerase inhibitory activity and cytotoxicity. Most of the compounds showed topo II alpha specific inhibitory activity. To clarify the mechanism of action of these compounds, the most potent compound (compound 14) of the synthesized analogues was further studied by testing its ATPase inhibitory activity and through molecular docking experiments. The results showed that the topo II alpha inhibitory activity of compound 14 was inversely proportional to ATP concentration. In the ATPase inhibitory test, ATP hydrolysis was reduced less efficiently by compound 14 (28.5 +/- 4.6%) than novobiocin (60.4 +/- 8.1%). Molecular docking study revealed compound 14 to have a stable binding pattern to the ATP-binding domain of human topo II. (C) 2011 Elsevier Masson SAS. All rights reserved.