4-氯-7-硝基喹啉 | 18436-76-5

• 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
• 中文名称: 4-氯-7-硝基喹啉
• 英文名称: 4-chloro-7-nitroquinoline
• 英文别名: 4-Chlor-7-nitro-chinolin
• CAS: 18436-76-5
• 化学式: C₉H₅ClN₂O₂
• 分子量: 208.604
• InChiKey: UPZGWWDLHRREJM-UHFFFAOYSA-N

物化性质

• 熔点：
  156-160 °C
• 沸点：
  351.4±22.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-氯-7-硝基喹啉 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 N⁴-(2-Diethylamino-ethyl)-quinoline-4,7-diamine
  参考文献：
  名称：

  Structure−Activity Relationships in 4-Aminoquinoline Antiplasmodials. The Role of the Group at the 7-Position

  摘要：

  Antiplasmodial activities versus the chloroquine sensitive D10 strain of Plasmodium falciparum of a series of N-1,N-1-diethyl-N-2-(4-quinolinyl)-1,2-ethanediamines with 11 different substituents at the 7-position on the quinoline ring have been investigated in vitro. Electron-withdrawing groups at the 7-position have been shown to lower the pK(a) of both the quinoline ring nitrogen atom and the tertiary amino nitrogen in the alkyl side chain. The quinoline nitrogen pK(a) ranges from 6.28 in the nitro derivative to 8.36 in the amino derivative, while the tertiary amino nitrogen has a pKa ranging between 7.65 in the trifluoromethyl derivative and 10.02 in the amino derivative. Calculation suggests that the resulting pH trapping of these compounds in the parasite food vacuole ranges between about 7% of that observed in chloroquine for the NO2 derivative and 97% in the amino derivative. A direct proportionality between antiplasmodial activity normalized for pH trapping and beta-hematin inhibitory activity was observed. Activity could not be correlated with any other observed physical parameter. The beta-hematin inhibitory activity of these derivatives appears to correlate with both the hematin-quinoline association constant and the electron-withdrawing capacity of the group at the 7-position (Hammett constant). For the compounds under investigation, the hematin association constant is in turn influenced by the lipophilicity of the group at the 7-position.

  DOI：

  10.1021/jm020858u
• 作为产物：
  描述：

  二乙基(3-硝基苯胺亚甲基)丙二酸 在 水 、 sodium hydroxide 、 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 8.6h， 生成 4-氯-7-硝基喹啉
  参考文献：
  名称：

  4-[(Quinolin-4-yl)amino]苯甲酰胺衍生物作为新型抗流感病毒药物的设计、合成、分子对接分析和生物学评价

  摘要：

  本研究设计合成了一系列4-[(quinolin-4-yl)amino]苯甲酰胺衍生物作为新型抗流感药物。进行细胞毒性试验、细胞病变效应试验和噬斑抑制试验以评估目标化合物的抗流感病毒 A/WSN/33 (H1N1) 活性。目标化合物G07在细胞病变效应试验 (EC 50 = 11.38 ± 1.89 µM) 和噬菌斑抑制试验 (IC 50 = 0.23 ± 0.15 µM)中均表现出显着的抗流感病毒 A/WSN/33 (H1N1) 活性。G07对其他三种不同的流感病毒株 A/PR/8 (H1N1)、A/HK/68 (H3N2) 和乙型流感病毒也表现出显着的抗流感病毒活性。根据核糖核蛋白重组试验结果，G07与核糖核蛋白相互作用良好，在100 µM时抑制率为80.65%。此外，根据最佳药效团 Hypo1 预测的 PA-PB1 抑制活性， G07表现出显着的活性靶标 RNA 聚合酶 PA-PB1

  DOI：

  10.3390/ijms23116307

文献信息

• Synthesis and Quantitative Structure-Activity Relationship of Dequalinium Analogs as K+ Channel Blockers: Investigations on the Role of the Substituent at Position 4 of the Quinoline Ring
  作者：Dimitrios Galanakis、Julie A. D. Calder、C. Robin Ganellin、Clive S. Owen、Philip M. Dunn

  DOI：10.1021/jm00018a013

  日期：1995.9

  group by other substituents (R4) and quantitative structure-activity relationship (QSAR) analysis on the resultant analogues have yielded a correlation between blocking potency and sigma R for R4 for seven of the compounds. The application of calculated electronic indices enabled the extension of the QSAR to compounds for which the appropriate sigma R values are not available, allowing all 13 analogues

  Dequalinium（4）是一种有效且选择性的小传导性Ca2 +活化K +通道的阻滞剂，这是一个重要但相对较少的研究课程。已显示的非氨苄基的4-NH2基团对阻断效能有显着贡献。在这项研究中，我们进一步研究了4-NH2基团的作用。该基团被其他取代基（R4）取代以及对所得类似物的定量结构-活性关系（QSAR）分析已对7个化合物的R4的封闭力和σR产生了相关性。计算出的电子指数的应用使QSAR可以扩展到没有适当sigma R值的化合物，从而使该系列的所有13个类似物都包括在相关性中。使用从AM1 MO计算得出的对模型化合物的电子指标进行的分析表明，封端效能与环N原子，ELUMO和EHOMO上的部分电荷相关。由于HOMO在所有化合物中的轨道都不相同，因此EHOMO相关性在质量上不一致。ELUMO相关性[pEMR = 1.19（+/- 0.21）ELUMO + 5.41（+/- 1.05），n =
• Substituted quinoline CCR5 receptor antagonists
  申请人：Schering Aktiengesellschaft

  公开号：US20040072818A1

  公开（公告）日：2004-04-15

  The present invention relates to CCR5 receptor antagonists of formulae (1a) or (1b): 1 enantiomers, diastereomers, salts and solvates thereof wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 are as defined herein. The invention further includes a method of CCR5-mediated disorders employing such compounds.

  本发明涉及公式（1a）或（1b）的CCR5受体拮抗剂：1对映体，对异构体，其盐和溶剂化物，其中R1、R2、R3、R4、R5和R7如本文所定义。本发明还包括一种利用这些化合物治疗CCR5介导的疾病的方法。
• Nitro and amino substituted topoisomerase agents
  申请人：——

  公开号：US20040102443A1

  公开（公告）日：2004-05-27

  The invention provides compounds of formula I: 1 wherein R 1 -R 9 , W, and X have any of the meanings defined in the specification and their pharmaceutically acceptable salts. The invention also provides pharmaceutical compositions. comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I, and therapeutic methods for treating cancer and infections using compounds of formula I.

  本发明提供了公式I的化合物：1其中R1-R9、W和X具有规范中定义的任何含义及其药学上可接受的盐。本发明还提供了包括公式I化合物的制药组合物，制备公式I化合物的过程，用于制备公式I化合物的中间体，以及使用公式I化合物治疗癌症和感染的治疗方法。
• Thioquinolone compounds which have useful pharmaceutical activity
  申请人：Zenyaku Kogyo Kabushiki Kaisha

  公开号：US05773449A1

  公开（公告）日：1998-06-30

  Disclosed is a thioquinolone derivative which exhibits highly selective antibacterial activity against Helicobacter pylori.

  公开了一种噻喹酮衍生物，对幽门螺杆菌具有高度选择性的抗菌活性。
• QUINOLINE DERIVATIVES FOR MODULATING DNA METHYLATION
  申请人：Phiasivongsa Pasit

  公开号：US20090285772A1

  公开（公告）日：2009-11-19

  Quinoline derivatives, particularly 4-anilinoquinoline derivatives, are provided. Such quinoline derivatives can be used for modulation of DNA methylation, such as effective inhibition of methylation of cytosine at the C-5 position, for example via selective inhibition of DNA methyltransferase DNMT1. Methods for synthesizing numerous 4-anilinoquinoline derivatives and for modulating DNA methylation are provided. Also provided are methods for formulating and administering these compounds or compositions to treat conditions such as cancer and hematological disorders.

  提供了喹啉衍生物，特别是4-苯胺基喹啉衍生物。这样的喹啉衍生物可用于调节DNA甲基化，例如通过选择性抑制DNA甲基转移酶DNMT1，有效抑制C-5位置的胞嘧啶甲基化。提供了合成多种4-苯胺基喹啉衍生物和调节DNA甲基化的方法。还提供了制剂和给药这些化合物或组合物以治疗癌症和血液疾病的方法。