2-Methoxy-6-(1-hydroxypentyl)-1,4-benzoquinone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methoxy-6-(1-hydroxypentyl)-1,4-benzoquinone
• 英文别名: Qeytvhcfimcnlt-uhfffaoysa-；2-(1-hydroxypentyl)-6-methoxycyclohexa-2,5-diene-1,4-dione
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: QEYTVHCFIMCNLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-甲氧基-6-(1'-羟基戊基)苯酚 在 potassium nitrososulfonate 、 sodium carbonate 作用下， 生成 2-Methoxy-6-(1-hydroxypentyl)-1,4-benzoquinone
  参考文献：
  名称：

  Isolation, Synthesis, and Structure−Activity Relationships of Bioactive Benzoquinones from Miconia lepidota from the Suriname Rainforest

  摘要：

  Bioactivity-directed fractionation of an EtOAc extract from the leaves of Miconia lepidota afforded the two benzoquinones 2-methoxy-6-heptyl-1,4-benzoquinone (1) and 2-methoxy-6-pentyl-1,4-benzoquinone (primin) (2). This is the first reported isolation of 1. Both quinones 1 and 2 exhibited activity toward mutant yeast strains based on Saccharomyces cerevisiae, indicative of their cytotoxicity and potential anticancer activity. A number of previously synthesized and new analogues were prepared and tested in the same strains. Compounds 1, 2, 2-methoxy-6-butyl-1,4-benzoquinone (5), and 2-methoxy-6-decyl-1,4-benzoquinone (6) were tested in two cytotoxicity assays. In the M109 tumor cell lines, quinones 1, 2, and 6 had an IC50 value of 10 mug/mL. In the A2780 cell line, compounds 1, 2 and 5 had IC50 values of 7.9, 2.9, and 3.2 mug/mL, respectively.

  DOI：

  10.1021/np000219r

表征谱图