6-[(4,5-dichloro-6-oxopyridazin-1-yl)methyl]-1H-pyrimidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-[(4,5-dichloro-6-oxopyridazin-1-yl)methyl]-1H-pyrimidine-2,4-dione
• 化学式: C₉H₆Cl₂N₄O₃
• 分子量: 289.078
• InChiKey: ZIYYGYBFDLZLKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  90.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 6-[(4,5-dichloro-6-oxopyridazin-1-yl)methyl]-1H-pyrimidine-2,4-dione 以 aq. phosphate buffer 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Identification of cytotoxic, glutathione-reactive moieties inducing accumulation of reactive oxygen species via glutathione depletion

  摘要：

  Reactive oxygen species (ROS) play an essential role in the survival and progression of cancer. Moderate oxidative stress drives proliferation, whereas high levels of ROS induce cytotoxicity. Compared to cancer cells, healthy cells often exhibit lower levels of oxidative stress. Elevation of cellular ROS levels by small molecules could therefore induce cancer-specific cytotoxicity. We have employed high-throughput phenotypic screening to identify inducers of ROS accumulation. We found 4,5-dihalo-2-methylpyridazin-3-one (DHMP) and 2,3,4,5(6)-tetrachloro-6(5)-methylpyridine (TCMP) moieties to strongly deplete GSH, to cause ROS accumulation and to induce cell death. Small molecules containing these fragments will most likely share the same properties and should therefore be carefully considered in the development of bioactive molecules. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.11.009