4-(3-Dimethylaminopropylamino)-7-nitrochinolin | 40107-17-3

• 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
• 英文名称: 4-(3-Dimethylaminopropylamino)-7-nitrochinolin
• 英文别名: N1,N1-dimethyl-N3-(7-nitro-4-quinolinyl)-1,3-propanediamine；N',N'-dimethyl-N-(7-nitro-4-quinolyl)propane-1,3-diamine；N',N'-dimethyl-N-(7-nitroquinolin-4-yl)propane-1,3-diamine
• CAS: 40107-17-3
• 化学式: C₁₄H₁₈N₄O₂
• 分子量: 274.323
• InChiKey: UOSZAJRVPAXWQM-UHFFFAOYSA-N

物化性质

• 沸点：
  458.2±40.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯-7-硝基喹啉 、 N,N-二甲基-1,3-二氨基丙烷 生成 4-(3-Dimethylaminopropylamino)-7-nitrochinolin
  参考文献：
  名称：

  Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins

  摘要：

  A series of isomeric 4-[[3-(dimethylamino)propyl]amino]nitroquinolines has been synthesized and evaluated as hypoxia-selective cytotoxins and as radioeensitizers of hypoxic cells. The compounds showed widely-differing hypersensitivity factors (ratios of cytotoxicity against wild-type and repair-deficient mammalian cells). Many compounds showed oxygen-sensitive bioreduction resulting in DNA alkylation, while others show oxygen-insensitive modes of action. Of the nitro isomers studied, the 5-nitro showed the greatest hypoxic selectivity. A series of ring-substituted analogues were then prepared, in an effort to lower its reduction potential of -286 mV. Structure-activity studies showed that the effects of substitution on reduction potential were complex, being mediated by electronic and steric effects on the nitro group, as well as by effects on quinoline pK(a). Two compounds of lower reduction potential, the 3- and 8-methyl analogues, showed improved selectivity (47- and 60-fold in a clonogenic assay). These two compounds also showed the highest ''in vitro therapeutic indices'' of the series as hypoxic cell radiosensitizers. Despite these favorable in vitro properties, neither compound had activity against hypoxic cells in SCCVII tumors when administered at 60% of the MTD.

  DOI：

  10.1021/jm00104a008

文献信息

• Method for the Fluorescent Detection of Nitroreductase Activity Using Nitro-Substituted Aromatic Compounds
  申请人：Smaill Jeffrey B.

  公开号：US20100173332A1

  公开（公告）日：2010-07-08

  A method utilising one or more fluorogenic probes, for the detection of nitroreductase activity. The non-fluorescent probes are reduced in the presence of nitroreductase to form fluorescent derivatives that may be detected using fluorescence spectroscopy. In particular, the method may be used to detect and/or identify a plurality of nitroreductase in a single test environment

  一种利用一个或多个荧光探针检测硝基还原酶活性的方法。非荧光探针在硝基还原酶存在下被还原成荧光衍生物，可以使用荧光光谱法检测。特别地，该方法可用于在单个测试环境中检测和/或鉴定多种硝基还原酶。