5-(4-nitrobenzyloxy)-1,4,4a,9a-tetrahydro-1,4-ethanoanthracene-9,10-dione | 1522974-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5-(4-nitrobenzyloxy)-1,4,4a,9a-tetrahydro-1,4-ethanoanthracene-9,10-dione
• 英文别名: 5-[(4-Nitrophenyl)methoxy]tetracyclo[10.2.2.02,11.04,9]hexadeca-4(9),5,7,13-tetraene-3,10-dione；5-[(4-nitrophenyl)methoxy]tetracyclo[10.2.2.02,11.04,9]hexadeca-4(9),5,7,13-tetraene-3,10-dione
• CAS: 1522974-99-7
• 化学式: C₂₃H₁₉NO₅
• 分子量: 389.408
• InChiKey: YZBHFEMOHJSPDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-nitrobenzyloxy)-1,4,4a,9a-tetrahydro-1,4-ethanoanthracene-9,10-dione 在 E_. coli nitroreductase 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 aq. phosphate buffer 为溶剂， 生成 1,4-Ethano-5-hydroxy-1,4-dihydro-9,10-anthraquinone
  参考文献：
  名称：

  A Small Molecule for Controlled Generation of Reactive Oxygen Species (ROS)

  摘要：

  Due to the short half-life of reactive oxygen species (ROS) such as a superoxide radical, controlled and localized generation of ROS is challenging. Here, we report a rationally designed small-molecule 1c that generates ROS only when triggered by a bacterial enzyme. We provide evidence for 1c predictably enhancing the intracellular superoxide radical in a model bacterium. Spatiotemporal control over ROS generation offered by 1c should help better understand stress responses in bacteria to increased ROS.

  DOI：

  10.1021/ol403300a
• 作为产物：
  描述：

  endo-1,4-Ethano-5-hydroxy-1,4,4a,9a-tetrahydro-9,10-anthraquinone 、 对硝基溴化苄 在 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以66%的产率得到5-(4-nitrobenzyloxy)-1,4,4a,9a-tetrahydro-1,4-ethanoanthracene-9,10-dione
  参考文献：
  名称：

  A Small Molecule for Controlled Generation of Reactive Oxygen Species (ROS)

  摘要：

  Due to the short half-life of reactive oxygen species (ROS) such as a superoxide radical, controlled and localized generation of ROS is challenging. Here, we report a rationally designed small-molecule 1c that generates ROS only when triggered by a bacterial enzyme. We provide evidence for 1c predictably enhancing the intracellular superoxide radical in a model bacterium. Spatiotemporal control over ROS generation offered by 1c should help better understand stress responses in bacteria to increased ROS.

  DOI：

  10.1021/ol403300a

文献信息

• A Small Molecule for Controlled Generation of Reactive Oxygen Species (ROS)
  作者：Allimuthu T. Dharmaraja、Harinath Chakrapani

  DOI：10.1021/ol403300a

  日期：2014.1.17

  Due to the short half-life of reactive oxygen species (ROS) such as a superoxide radical, controlled and localized generation of ROS is challenging. Here, we report a rationally designed small-molecule 1c that generates ROS only when triggered by a bacterial enzyme. We provide evidence for 1c predictably enhancing the intracellular superoxide radical in a model bacterium. Spatiotemporal control over ROS generation offered by 1c should help better understand stress responses in bacteria to increased ROS.