2,4-dimethyl-6-methoxy-8-nitroquinoline | 54232-17-6

• 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: 2,4-dimethyl-6-methoxy-8-nitroquinoline
• 英文别名: 2,4-Dimethyl-6-methoxy-8-nitrochinolin；6-methoxy-2,4-dimethyl-8-nitro-quinoline；6-methoxy-2,4-dimethyl-8-nitroquinoline
• CAS: 54232-17-6
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: JDBHMVMJHGROBI-UHFFFAOYSA-N

物化性质

• 熔点：
  188-191 °C
• 沸点：
  389.5±37.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2,4-dimethyl-6-methoxy-8-nitroquinoline 、 盐酸二甲胺 以 乙醇 为溶剂， 反应 48.0h， 以72%的产率得到2-(6-methoxy-4-methyl-8-nitroquinolin-2-yl)-N,N-dimethylethanamine;hydrochloride
  参考文献：
  名称：

  Synthesis of 2,4-disubstituted 6-methoxy-8-aminoquinoline analogs as potential antiparasitics

  摘要：

  A series of 2,4-disubstituted 8-aminoquinoline analogues were synthesized and evaluated against Plasmodium berghei in mice and Leishmania donovani in hamsters. 8-[[6-(Diethylamino)hexyl]amino]-2-ethyl-6-methoxy-4-methylquinoline (8a) possessed significant activity against L. donovani. 2-Ethyl-4-methylprimaquine (7a) was evaluated against Plasmodium cynomolgi in rhesus monkey and found to have activity equal to that of primaquine.

  DOI：

  10.1021/jm00179a023
• 作为产物：
  描述：

  3-戊烯-2-酮 、 2-硝基-4-甲氧基苯胺 在 arsenic(V) oxide 、 磷酸 作用下， 生成 2,4-dimethyl-6-methoxy-8-nitroquinoline
  参考文献：
  名称：

  Synthesis of 2,4-disubstituted 6-methoxy-8-aminoquinoline analogs as potential antiparasitics

  摘要：

  A series of 2,4-disubstituted 8-aminoquinoline analogues were synthesized and evaluated against Plasmodium berghei in mice and Leishmania donovani in hamsters. 8-[[6-(Diethylamino)hexyl]amino]-2-ethyl-6-methoxy-4-methylquinoline (8a) possessed significant activity against L. donovani. 2-Ethyl-4-methylprimaquine (7a) was evaluated against Plasmodium cynomolgi in rhesus monkey and found to have activity equal to that of primaquine.

  DOI：

  10.1021/jm00179a023

文献信息

• Process for production of 8-NHR quinolines
  申请人：The United States of America as represented by the Secretary of the Army

  公开号：US04167638A1

  公开（公告）日：1979-09-11

  An improved process for producing 8-NHR quinolines from 8-aminoquinolines disclosed. The process comprises reacting 8-aminoquinolines with a substituted alkyl halide in the presence of an amine having a boiling point of 80.degree.-90.degree. C. The amine functions as an acid acceptor whereby the amine salt formed may be efficiently separated from the 8-NHR quinoline formed without expensive or time consuming purification steps. The reaction may be carried out in the presence of a solvent such as an alcohol.

  一种改进的方法用于从8-氨基喹啉制备8-NHR喹啉。该方法包括在存在沸点为80度至90度的胺的情况下，将8-氨基喹啉与取代烷基卤化物反应。胺起到酸受体的作用，从而形成的胺盐可以在无需昂贵或耗时的纯化步骤的情况下有效地与形成的8-NHR喹啉分离。反应可以在存在溶剂（如醇类）的情况下进行。
• CORROLLY F. I.; BERRANG B. D.; LINN C. P., J. MED. CHEM., 1980, 23, NO 5, 581-584
  作者：CORROLLY F. I.、 BERRANG B. D.、 LINN C. P.

  DOI：——

  日期：——
• US4167638A
  申请人：——

  公开号：US4167638A

  公开（公告）日：1979-09-11
• Synthesis of 2,4-disubstituted 6-methoxy-8-aminoquinoline analogs as potential antiparasitics
  作者：F. Ivy Carroll、Bertold D. Berrang、C. Preston Linn

  DOI：10.1021/jm00179a023

  日期：1980.5

  A series of 2,4-disubstituted 8-aminoquinoline analogues were synthesized and evaluated against Plasmodium berghei in mice and Leishmania donovani in hamsters. 8-[[6-(Diethylamino)hexyl]amino]-2-ethyl-6-methoxy-4-methylquinoline (8a) possessed significant activity against L. donovani. 2-Ethyl-4-methylprimaquine (7a) was evaluated against Plasmodium cynomolgi in rhesus monkey and found to have activity equal to that of primaquine.