2-(15-bromopentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone | 1251831-78-3

• 英文名称: 2-(15-bromopentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone
• CAS: 1251831-78-3
• 化学式: C₂₄H₃₉BrO₄
• 分子量: 471.475
• InChiKey: CWDHKZCFARDVMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  29.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(15-bromopentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone 在 sodium dithionite 、 水 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria

  摘要：

  Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.104
• 作为产物：
  描述：

  2,3-二甲氧基-5-甲基-1,4-苯醌 在 4-二甲氨基吡啶 、 ammonium persulfate 、 silver nitrate 、 三乙胺 、 sodium bromide 作用下， 以 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 12.5h， 生成 2-(15-bromopentadecyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone
  参考文献：
  名称：

  Biological evaluation of new mimetics of annonaceous acetogenins: Alteration of right scaffold by click linkage with aromatic functionalities

  摘要：

  A small library of analogues of annonaceous acetogenins through click linkage with aromatic moieties is established using a convergent modular fragment-assembly approach. These analogues exhibited low micromolar inhibitory activities against the proliferation of several human cancer cell lines. Structure-activity relationship (SAR) of these analogues indicates that replacement of the methoxy groups of ubiquinone ring with methyl groups is proved to be a useful strategy for improving the anticancer activity of quinone-acetogenin hybrids. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.062