2,5-bis<(2-hydroxyethyl)amino>-3,6-dichloro-1,4-benzoquinone | 28857-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis<(2-hydroxyethyl)amino>-3,6-dichloro-1,4-benzoquinone
• 英文别名: 2,5-dichloro-3,6-bis(2-hydroxyethylamino)cyclohexa-2,5-diene-1,4-dione；2,5-bis[(2-hydroxyethyl)amino]-3,6-dichloro-1,4-benzoquinone
• CAS: 28857-12-7
• 化学式: C₁₀H₁₂Cl₂N₂O₄
• 分子量: 295.122
• InChiKey: SPCMVBSYISBCEI-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168 °C(Solv: ethanol (64-17-5))
• 沸点：
  466.5±45.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-bis<(2-hydroxyethyl)amino>-3,6-dichloro-1,4-benzoquinone 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 2,5-bis<<2-<<carbamoyl>oxy>ethyl>amino>-3,6-dichloro-1,4-benzoquinone
  参考文献：
  名称：

  Synthesis and testing of quinone-based bis(2,2-dimethyl-1-aziridinyl)phosphinyl carbamates as radiation-potentiating antitumor agents

  摘要：

  Two new drug candidates, in which a quinonoid moiety is linked to the reactive bis(2,2-dimethyl-1-aziridinyl)phosphinyl function, have been prepared and tested in vivo for antitumor activity and in vitro as potentiators of the cytotoxic effect of X-irradiation. Without irradiation only moderate effectiveness against leukemia P-388 in mice was exhibited by one of the quinonoid compounds that had sufficient water solubility to be used in the in vivo screening. However, both compounds were shown to potentiate the effect of X-irradiation in vitro by a colony-forming cell culture assay under hypoxic conditions.

  DOI：

  10.1021/jm00401a028
• 作为产物：
  描述：

  四氯苯醌 、 C.I.酸性橙108 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以72.8%的产率得到2,5-bis<(2-hydroxyethyl)amino>-3,6-dichloro-1,4-benzoquinone
  参考文献：
  名称：

  Synthesis and testing of quinone-based bis(2,2-dimethyl-1-aziridinyl)phosphinyl carbamates as radiation-potentiating antitumor agents

  摘要：

  Two new drug candidates, in which a quinonoid moiety is linked to the reactive bis(2,2-dimethyl-1-aziridinyl)phosphinyl function, have been prepared and tested in vivo for antitumor activity and in vitro as potentiators of the cytotoxic effect of X-irradiation. Without irradiation only moderate effectiveness against leukemia P-388 in mice was exhibited by one of the quinonoid compounds that had sufficient water solubility to be used in the in vivo screening. However, both compounds were shown to potentiate the effect of X-irradiation in vitro by a colony-forming cell culture assay under hypoxic conditions.

  DOI：

  10.1021/jm00401a028

文献信息

• Design, Synthesis and Structure of Novel Para-Quinones and their Antibacterial Activity
  作者：Komala Pandurangan、Kevin D. Murnaghan、Aurora Walshe、Helge Müller-Bunz、Francesca Paradisi、Grace G. Morgan

  DOI：10.1111/j.1747-0285.2011.01187.x

  日期：2011.11

  Eight new para‐quinones and one known analogue have been synthesized from p‐chloranil. Five have been structurally characterized by single crystal diffraction, and a range of ligand folding is observed. All nine have been tested for their potency towards Gram(+) S. aureus and Gram(−) E. coli. Quinones 3, 6, 7 and 8 have shown activity towards S. aureus and quinones 3 and 8 also show good activity towards E. coli.
• ZHANG, SHOUFANG;EARLE, JULIE;MACDIARMID, JOAN;BARDOS, THOMAS J., J. MED. CHEM., 31,(1988) N 6, 1240-1244
  作者：ZHANG, SHOUFANG、EARLE, JULIE、MACDIARMID, JOAN、BARDOS, THOMAS J.

  DOI：——

  日期：——
• Synthesis and testing of quinone-based bis(2,2-dimethyl-1-aziridinyl)phosphinyl carbamates as radiation-potentiating antitumor agents
  作者：Shoufang Zhang、Julie Earle、Joan MacDiarmid、Thomas J. Bardos

  DOI：10.1021/jm00401a028

  日期：1988.6

  Two new drug candidates, in which a quinonoid moiety is linked to the reactive bis(2,2-dimethyl-1-aziridinyl)phosphinyl function, have been prepared and tested in vivo for antitumor activity and in vitro as potentiators of the cytotoxic effect of X-irradiation. Without irradiation only moderate effectiveness against leukemia P-388 in mice was exhibited by one of the quinonoid compounds that had sufficient water solubility to be used in the in vivo screening. However, both compounds were shown to potentiate the effect of X-irradiation in vitro by a colony-forming cell culture assay under hypoxic conditions.