4-chloro-2-methyl-5-nitroquinoline | 145363-63-9

• 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
• 英文名称: 4-chloro-2-methyl-5-nitroquinoline
• 英文别名: 2-Methyl-4-chlor-5-nitrochinolin；4-Chlor-2-methyl-5-nitro-chinolin
• CAS: 145363-63-9
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: IGXACOMJGSJFJU-UHFFFAOYSA-N

物化性质

• 熔点：
  111-113 °C
• 沸点：
  344.8±37.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-2-methyl-5-nitroquinoline 生成 5-氨基喹哪啶
  参考文献：
  名称：

  SINHA B. K.; PHILEN R. M.; SATO R.; CYSYK R. L., J. MED. CHEM. , 1977, 20, NO 11, 1528-1531

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methyl-5-nitro-1H-quinolin-4-one 、 三氯氧磷 以50%的产率得到
  参考文献：
  名称：

  SINHA B. K.; PHILEN R. M.; SATO R.; CYSYK R. L., J. MED. CHEM. , 1977, 20, NO 11, 1528-1531

  摘要：

  DOI：

文献信息

• Synthesis of 4,5-Bis(Dimethylamino)Quinolines and the Dual Direction of their Protonation
  作者：E. A. Shmoilova、O. V. Dyablo、A. F. Pozharskii

  DOI：10.1007/s10593-013-1380-4

  日期：2013.12

  A study on the synthesis of derivatives of 4,5-bis(dimethylamino)quinoline, which is a quinoline analog of 1,8-bis(dimethylamino)naphthalene (also known by its trade name Proton Sponge) was carried out. The first two representatives of this series were obtained. Depending on the aggregate state, solvent, and structural features, these compounds may be protonated either at the quinoline heteroatom or peri-NMe2 groups.
• Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins
  作者：William A. Denny、Graham J. Atwell、Peter B. Roberts、Robert F. Anderson、Maruta Boyd、Colin J. L. Lock、William R. Wilson

  DOI：10.1021/jm00104a008

  日期：1992.12

  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.
• 104. Nitration of 4-chloro- and 4-hydroxy-quinaldine
  作者：Barbara E. Halcrow、William O. Kermack

  DOI：10.1039/jr9450000415

  日期：——
• SINHA B. K.; PHILEN R. M.; SATO R.; CYSYK R. L., J. MED. CHEM. <JMCM-AR>, 1977, 20, NO 11, 1528-1531
  作者：SINHA B. K.、 PHILEN R. M.、 SATO R.、 CYSYK R. L.

  DOI：——

  日期：——