2-Methyl-3-nitro-4-chloroquinoline | 79358-29-5

• 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: 2-Methyl-3-nitro-4-chloroquinoline
• 英文别名: 4-chloro-2-methyl-3-nitroquinoline；4-chloro-2-methyl-3-nitro-quinoline；4-Chlor-2-methyl-3-nitro-chinolin
• CAS: 79358-29-5
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: SECDHFOURHYAKP-UHFFFAOYSA-N

物化性质

• 熔点：
  79-82 °C(Solv: ethanol (64-17-5))
• 沸点：
  332.5±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：

  2-Methyl-3-nitro-4-chloroquinoline 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 3-氨基-2-甲基喹啉
  参考文献：
  名称：

  Koenigs; Freund, Chemische Berichte, 1941, vol. 74, p. 1085,1087

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methyl-3-nitro-4-hydroxyquinoline 在 五氯化磷 、 三氯氧磷 作用下， 以82.5%的产率得到2-Methyl-3-nitro-4-chloroquinoline
  参考文献：
  名称：

  Ibrahim, E. S.; Badawi, M. El; Amen, M. A., Egyptian Journal of Chemistry, 1994, vol. 37, # 2, p. 197 - 205

  摘要：

  DOI：

文献信息

• 349. Nitrosoacylarylamines. Part V. The nitrosation of 3-acetamido-4-quinolones and -quinaldones
  作者：W. J. Adams、D. H. Hey

  DOI：10.1039/jr9510001521

  日期：——
• Takahashi; Senda, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1952, vol. 72, p. 1109
  作者：Takahashi、Senda

  DOI：——

  日期：——
• Internuclear cyclisation. Part VIII. Naphth[3 : 2 : 1-cd]oxindoles
  作者：R. A. Abramovitch、D. H. Hey

  DOI：10.1039/jr9540001697

  日期：——
• 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.
• Kato, Tetsuzo; Katagiri, Nobuya; Wagai, Akihiro, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 4, p. 1069 - 1075
  作者：Kato, Tetsuzo、Katagiri, Nobuya、Wagai, Akihiro

  DOI：——

  日期：——