2,6-bis(phenylselanyl)-3,5-dimethoxy-1,4-benzoquinone | 1414286-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-bis(phenylselanyl)-3,5-dimethoxy-1,4-benzoquinone
• 英文别名: 2,6-Dimethoxy-3,5-bis(phenylselanyl)cyclohexa-2,5-diene-1,4-dione；2,6-dimethoxy-3,5-bis(phenylselanyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 1414286-75-1
• 化学式: C₂₀H₁₆O₄Se₂
• 分子量: 478.265
• InChiKey: YZRMBZDQPRWCBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 、 2,6-dibromo-3,5-dimethoxy-1,4-benzoquinone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.25h， 以34.1%的产率得到2,6-bis(phenylselanyl)-3,5-dimethoxy-1,4-benzoquinone
  参考文献：
  名称：

  Selenium- and tellurium-containing redox modulators with distinct activity against macrophages: possible implications for the treatment of inflammatory diseases

  摘要：

  Various selenium- and tellurium-containing molecules are able to modulate the intracellular redox state of cells, an effect which may be used for the (selective) targeting of cancer cells, which are naturally under oxidative stress (OS). As macrophages also generate an environment rich in Reactive Oxygen WSpecies (ROS) and nitric oxide ((NO)-N-center dot), they may represent an additional, prime target for such redox-modulating agents. A range of selenium and tellurium-containing quinones have therefore been synthesized and subsequently tested in macrophage culture. The tellurium agents were generally cytotoxic at very low concentrations, and their mode of action seemed to involve the upregulation of intracellular ROS levels. This redox-modulating effect was confirmed by simple yeast-based chemogenetic analysis in conjunction with in vitro redox assays and electrochemistry. Together, these studies point towards an intracellular build-up of superoxide radicals as the most likely cause of toxicity. In contrast, some of the selenium derivatives were less toxic and exerted a pronounced inhibitory effect on the formation of lipopolysaccharide-induced (NO)-N-center dot production. Whilst the Te-analogues therefore may enable the resolute, effective and fairly selective targeting of macrophages, the selenium agents could act less severely, but equally effectively by interfering with inflammatory signalling molecules. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.021

文献信息

• Selenium- and tellurium-containing redox modulators with distinct activity against macrophages: possible implications for the treatment of inflammatory diseases
  作者：Mandy Doering、Britta Diesel、Martin C.H. Gruhlke、Uma M. Viswanathan、Dominika Mániková、Miroslav Chovanec、Torsten Burkholz、Alan J. Slusarenko、Alexandra K. Kiemer、Claus Jacob

  DOI：10.1016/j.tet.2012.09.021

  日期：2012.12

  Various selenium- and tellurium-containing molecules are able to modulate the intracellular redox state of cells, an effect which may be used for the (selective) targeting of cancer cells, which are naturally under oxidative stress (OS). As macrophages also generate an environment rich in Reactive Oxygen WSpecies (ROS) and nitric oxide ((NO)-N-center dot), they may represent an additional, prime target for such redox-modulating agents. A range of selenium and tellurium-containing quinones have therefore been synthesized and subsequently tested in macrophage culture. The tellurium agents were generally cytotoxic at very low concentrations, and their mode of action seemed to involve the upregulation of intracellular ROS levels. This redox-modulating effect was confirmed by simple yeast-based chemogenetic analysis in conjunction with in vitro redox assays and electrochemistry. Together, these studies point towards an intracellular build-up of superoxide radicals as the most likely cause of toxicity. In contrast, some of the selenium derivatives were less toxic and exerted a pronounced inhibitory effect on the formation of lipopolysaccharide-induced (NO)-N-center dot production. Whilst the Te-analogues therefore may enable the resolute, effective and fairly selective targeting of macrophages, the selenium agents could act less severely, but equally effectively by interfering with inflammatory signalling molecules. (C) 2012 Elsevier Ltd. All rights reserved.