N¹,N¹-dimethyl-N²-(6-trifluoromethyl-1,4-dioxido-1,2,4-benzotriazin-3-yl)-1,2-ethanediamine | 736139-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: N¹,N¹-dimethyl-N²-(6-trifluoromethyl-1,4-dioxido-1,2,4-benzotriazin-3-yl)-1,2-ethanediamine
• CAS: 736139-13-2
• 化学式: C₁₂H₁₄F₃N₅O₂
• 分子量: 317.271
• InChiKey: SERTWQMHIPRLGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.49
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82.04
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  6-trifluoromethyl-1,2,4-benzotriazin-3-amine 1-oxide 在 双氧水 、 三氟乙酸 、 三氟乙酸酐 、 sodium nitrite 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 12.0h， 生成 N¹,N¹-dimethyl-N²-(6-trifluoromethyl-1,4-dioxido-1,2,4-benzotriazin-3-yl)-1,2-ethanediamine
  参考文献：
  名称：

  Oxidation of 2-Deoxyribose by Benzotriazinyl Radicals of Antitumor 3-Amino-1,2,4-benzotriazine 1,4-Dioxides

  摘要：

  Tirapazamine (3-amino-1,2,4-benzotriazine 1,4-dioxide) is the lead bioreductive drug in clinical trials as an anticancer agent to kill refractory hypoxic cells of solid tumors. It has long been known that, upon metabolic one-electron reduction, tirapazamine induces lethal DNA double strand breaks in hypoxic cells. These strand breaks arise from radical damage to the ribose moiety of DNA, and in this pulse radiolysis and product analysis study we examine mechanistic aspects of the dual function of tirapazamine and analogues in producing radicals of sufficient power to oxidize 2-deoxyribose to form radicals, as well as the ability of the compounds to oxidize the resulting deoxyribose radicals to generate the strand breaks. Both the rate of oxidation of 2-deoxyribose and the radical yield increase with the one-electron reduction potentials of the putative benzotriazinyl radicals formed from the benzotriazine 1,4-dioxides. Subsequent oxidation of the 2-deoxyribose radicals by the benzotriazine 1,4-dioxides and 1-oxides proceeds through adduct formation followed by breakdown to form the radical anions of both species. The yield of the radical anions increases with increasing one-electron reduction potentials of the compounds. We have previously presented evidence that oxidizing benzotriazinyl radicals are formed following one-electron reduction of the benzotriazine 1,4-dioxides. The reactions reported in this work represent the kinetic basis of a short chain reaction leading to increased oxidation of 2-deoxyribose, a process which is dependent on the one-electron reduction potential of the benzotriazinyl radicals that are above a threshold value of ca. 1.24 V.

  DOI：

  10.1021/ja048740l