[(9-{[3-(二甲氨基)丙基]氨基}-1-硝基吖啶-4-基)亚氨基]二乙烷-2,1-二基二乙酸酯 | 107210-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: [(9-{[3-(二甲氨基)丙基]氨基}-1-硝基吖啶-4-基)亚氨基]二乙烷-2,1-二基二乙酸酯
• 英文名称: 4--9-<3-dimethylaminopropylamino>-1-nitroacridine
• 英文别名: 4-(bis(2-acetoxyethyl)amino)-9-(3-dimethylaminopropylamino)-1-nitroacridine；2,2'-((9-((3-(Dimethylamino)propyl)amino)-1-nitro-4-acridinyl)imino)bisethanol diacetate；2-[2-acetyloxyethyl-[9-[3-(dimethylamino)propylamino]-1-nitroacridin-4-yl]amino]ethyl acetate
• CAS: 107210-39-9
• 化学式: C₂₆H₃₃N₅O₆
• 分子量: 511.578
• InChiKey: KBGYNIMZFLTVQC-UHFFFAOYSA-N

物化性质

• 熔点：
  101 °C
• 沸点：
  684.9±55.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(9-{[3-(二甲氨基)丙基]氨基}-1-硝基吖啶-4-基)亚氨基]二乙烷-2,1-二基二乙酸酯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以85%的产率得到4--9-(3-dimethylaminopropylamino)-1-nitroacridine
  参考文献：
  名称：

  Chambers, David; Denny, William A., Journal of the Chemical Society. Perkin transactions I, 1986, p. 1055 - 1060

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[(2,4-二硝基苯基)-(2-羟乙基)氨基]乙醇 在 吡啶 、 sodium sulfide 、 copper diacetate 、 sulfur 、 三氯氧磷 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.25h， 生成 [(9-{[3-(二甲氨基)丙基]氨基}-1-硝基吖啶-4-基)亚氨基]二乙烷-2,1-二基二乙酸酯
  参考文献：
  名称：

  Chambers, David; Denny, William A., Journal of the Chemical Society. Perkin transactions I, 1986, p. 1055 - 1060

  摘要：

  DOI：

文献信息

• Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine
  作者：William R. Wilson、Robert F. Anderson、William A. Denny

  DOI：10.1021/jm00121a006

  日期：1989.1

  The nitroacridine derivative 9-[[3-(dimethylamino)propyl]amino]-1-nitroacridine (nitracrine) is selectively cytotoxic to hypoxic tumor cells in culture. However, the compound undergoes reductive metabolism too rapidly, with the reduction not being sufficiently inhibited by molecular oxygen in aerobic tissues, for it to demonstrate the same activity in vivo. In a search for derivatives with lower reduction potentials, we have synthesized and evaluated a series of derivatives bearing 4-substituents with a wide range of electronic properties. The one-electron reduction potentials (E(1] of these compounds, when compared under conditions of equivalent ionization, were highly correlated with sigma p values. However, at pH 7 the influence of substituent electronic properties was modified by prototrophic equilibria, with the basic nature of the acridine limiting the extent to which ring substituent electronic effects can be used to modulate reduction potential of the 1-nitro group. Nevertheless, comparison of the kinetics of the killing of AA8 cells under hypoxia suggests that some metabolic stabilization of the compounds can be achieved by the use of electron-donating substituents, with such compounds retaining the hypoxia-selective toxicity of nitracrine in cell culture. However, the 4-substituted nitracrines show no clear relationship between E(1) and cytotoxic potency, in distinct contrast to simpler nitroheterocycles such as nitroimidazoles.
• CHAMBERS D.; DANNY W. A., J. CHEM. SOC. PERKIN TRANS.,(1986) N 6, 1055-1060
  作者：CHAMBERS D.、 DANNY W. A.

  DOI：——

  日期：——