N,N-bis(2-bromoethyl)-4-nitroaniline | 122567-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-bis(2-bromoethyl)-4-nitroaniline
• CAS: 122567-47-9
• 化学式: C₁₀H₁₂Br₂N₂O₂
• 分子量: 352.025
• InChiKey: DHKBGSHNGQVYCU-UHFFFAOYSA-N

物化性质

• 沸点：
  428.5±40.0 °C(Predicted)
• 密度：
  1.772±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-bis(2-bromoethyl)-4-nitroaniline 在 5%-palladium/activated carbon 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  一种具有Cu2+识别功能的双光子荧光探针及 其制备方法和用途

  摘要：

  本发明公开了一种具有Cu 2+ 识别功能的双光子荧光探针及其制备方法和用途，其中具有Cu 2+ 识别功能的双光子荧光探针的结构式为： 本发明双光子荧光探针在紫外‑可见光区可以选择性地识别Cu 2+ ，不受其它金属离子的干扰，实验证明探针分子与铜离子形成的配合物具有良好的水溶性和生物相容性。生物学实验表明，本发明双光子荧光探针可以透过细胞膜，靶向在细胞线粒体和斑马鱼的肝部及胃部，显示黄绿色荧光，加入外源性铜离子后，探针在生物体内的荧光几乎完全淬灭，随着与Cu 2+ 配位能力更强的组氨酸加入，探针HL被释放，荧光基本恢复。这一研究结果的发现，本发明双光子荧光探针作为Cu 2+ 识别荧光探针具有重要的实用价值。

  公开号：

  CN107082751B
• 作为产物：
  描述：

  N,N-bis<2-<(methylsulfonyl)oxy>ethyl>-4-nitroaniline 在 sodium bromide 、 sodium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 N,N-bis(2-bromoethyl)-4-nitroaniline
  参考文献：
  名称：

  Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines

  摘要：

  A series of aniline mustards with a wide range of electron-donating and -withdrawing substituents in the 3- and 4-positions has been synthesized and evaluated for cytotoxicity in cell culture to examine the potential of using nitro group deactivated nitrogen mustards for the design of novel hypoxia-selective anticancer drugs (Denny, W. A.; Wilson, W. R. J. Med. Chem. 1986, 29, 879). Hydrolytic half-lives in tissue culture media, determined by bioassay against a cell line (UV4) defective in the repair of DNA interstrand cross-links showed the expected dependence on the Hammett electronic parameter, sigma, varying from 0.13 h for the 4-amino analogue to greater than 100 h for analogues with strongly electron-withdrawing substituents. Cytotoxic potencies in aerobic UV4 cultures showed a similar dependence on sigma. This dependence predicted that the 4-nitroaniline mustard would be 7200-fold less potent than its potential six-electron reduction product, the 4-amino compound, in growth inhibition assays using a 1-h drug exposure. The measured differential was much lower (225-fold) because of the instability of the latter compound, but a differential of 17,500-fold was observed in the initial rate of killing by using a clonogenic assay. The potential for formation of reactive mustards by reduction to the amine or hydroxylamine was demonstrated by the 4-nitroso compound, which had an aerobic toxicity similar to that of the amine. Although these features confirmed the original rationale, the 3-nitro- and 4-nitroaniline mustards had only minimal hypoxic selectivity against UV cells. Toxicity to hypoxic cells appears to be limited by the low reduction potentials of these compounds and consequent lack of enzymatic nitroreduction. However, this study has demonstrated that nitro groups can be used to latentiate aromatic nitrogen mustards and indicates that examples with higher reduction potentials could provide useful hypoxia-selective therapeutic agents.

  DOI：

  10.1021/jm00163a019

文献信息

• Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines
  作者：Brian D. Palmer、William R. Wilson、Susan M. Pullen、William A. Denny

  DOI：10.1021/jm00163a019

  日期：1990.1

  A series of aniline mustards with a wide range of electron-donating and -withdrawing substituents in the 3- and 4-positions has been synthesized and evaluated for cytotoxicity in cell culture to examine the potential of using nitro group deactivated nitrogen mustards for the design of novel hypoxia-selective anticancer drugs (Denny, W. A.; Wilson, W. R. J. Med. Chem. 1986, 29, 879). Hydrolytic half-lives in tissue culture media, determined by bioassay against a cell line (UV4) defective in the repair of DNA interstrand cross-links showed the expected dependence on the Hammett electronic parameter, sigma, varying from 0.13 h for the 4-amino analogue to greater than 100 h for analogues with strongly electron-withdrawing substituents. Cytotoxic potencies in aerobic UV4 cultures showed a similar dependence on sigma. This dependence predicted that the 4-nitroaniline mustard would be 7200-fold less potent than its potential six-electron reduction product, the 4-amino compound, in growth inhibition assays using a 1-h drug exposure. The measured differential was much lower (225-fold) because of the instability of the latter compound, but a differential of 17,500-fold was observed in the initial rate of killing by using a clonogenic assay. The potential for formation of reactive mustards by reduction to the amine or hydroxylamine was demonstrated by the 4-nitroso compound, which had an aerobic toxicity similar to that of the amine. Although these features confirmed the original rationale, the 3-nitro- and 4-nitroaniline mustards had only minimal hypoxic selectivity against UV cells. Toxicity to hypoxic cells appears to be limited by the low reduction potentials of these compounds and consequent lack of enzymatic nitroreduction. However, this study has demonstrated that nitro groups can be used to latentiate aromatic nitrogen mustards and indicates that examples with higher reduction potentials could provide useful hypoxia-selective therapeutic agents.
• 一种具有Cu2+识别功能的双光子荧光探针及 其制备方法和用途
  申请人：安徽大学

  公开号：CN107082751B

  公开（公告）日：2018-10-23

  本发明公开了一种具有Cu 2+ 识别功能的双光子荧光探针及其制备方法和用途，其中具有Cu 2+ 识别功能的双光子荧光探针的结构式为： 本发明双光子荧光探针在紫外‑可见光区可以选择性地识别Cu 2+ ，不受其它金属离子的干扰，实验证明探针分子与铜离子形成的配合物具有良好的水溶性和生物相容性。生物学实验表明，本发明双光子荧光探针可以透过细胞膜，靶向在细胞线粒体和斑马鱼的肝部及胃部，显示黄绿色荧光，加入外源性铜离子后，探针在生物体内的荧光几乎完全淬灭，随着与Cu 2+ 配位能力更强的组氨酸加入，探针HL被释放，荧光基本恢复。这一研究结果的发现，本发明双光子荧光探针作为Cu 2+ 识别荧光探针具有重要的实用价值。