7,8-二氯-6-硝基喹啉 | 261764-93-6

• 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
• 中文名称: 7,8-二氯-6-硝基喹啉
• 英文名称: 7,8-dichloro-6-nitroquinoline
• CAS: 261764-93-6
• 化学式: C₉H₄Cl₂N₂O₂
• 分子量: 243.049
• InChiKey: BDIAHZWYGIWLNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  388.8±37.0 °C(Predicted)
• 密度：
  1.593±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  7,8-二氯-6-硝基喹啉 在 palladium on activated charcoal 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以95%的产率得到6-氨基喹啉
  参考文献：
  名称：

  取代氨基喹啉作为制备芳族 N-三环体系的有用中间体的合成

  摘要：

  描述了一种合成新的取代单和二氨基喹啉的有效方法。两种已知的喹啉 7,8-二氯-6-硝基喹啉 (1) 和 7,8-二氯-6-硝基氢喹啉-4-酮 (9) 被用作关键中间体。

  DOI：

  10.3987/com-06-10782
• 作为产物：
  描述：

  N-(2,3-二氯苯基)乙酰胺 在 arsenic pentoxide hydrate 、 硫酸 、 potassium nitrate 作用下， 反应 9.0h， 生成 7,8-二氯-6-硝基喹啉
  参考文献：
  名称：

  Design, synthesis, and preliminary in vitro and in silico antiviral activity of [4,7]phenantrolines and 1-oxo-1,4-dihydro-[4,7]phenantrolines against single-stranded positive-sense RNA genome viruses

  摘要：

  Following the antiviral screening of a wide series of new angular and linear N-tricyclic systems both in silico and in vitro, the [4,7]phenantroline nucleus emerged as a new ring system endowed with activity against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). Here, we report our new pathway to the synthesis of this nucleus and of several related derivatives, as well as the results of both cell-based antiviral assays and molecular dynamics simulations. In the antiviral screening, several compounds (9 and 16-20) showed to be fairly active against BVDV, CVB-2, and Polio I (EC50, 6-25 mu M). According to molecular dynamics simulations, compounds (15) and (17) emerged for its potency against the HCV NS5B, with a calculated IC50 of 11-12 mu M. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.005

文献信息

• Quinoline tricyclic derivatives. Design, synthesis and evaluation of the antiviral activity of three new classes of RNA-dependent RNA polymerase inhibitors
  作者：Antonio Carta、Irene Briguglio、Sandra Piras、Paola Corona、Giampiero Boatto、Maria Nieddu、Paolo Giunchedi、Maria Elena Marongiu、Gabriele Giliberti、Filippo Iuliano、Sylvain Blois、Cristina Ibba、Bernardetta Busonera、Paolo La Colla

  DOI：10.1016/j.bmc.2011.10.009

  日期：2011.12

  CVB-5, Reo-1 and RSV. However, derivatives belonging to all classes showed activity against BVDV. Among the most potent were the bis-triazoloquinoline 1m, the imidazoquinolines 2e and 2h, and the pyridoquinoxalines 4h, 4j and 5n (EC50 range 1–5 μM). When tested in a replicon assay, compound 2h was the sole derivative to also display anti-HCV activity (EC50 = 3.1 μM). In enzyme assays, 1m, 2h, 5m and 5n

  在这项研究中，合成了三类新的线性N-三环化合物，它们是由喹啉核与1,2,3-三唑，咪唑或吡嗪缩合而得到的，获得了三唑并[4,5- g ]喹啉，咪唑并[4]。分别是，5-5- g喹啉和吡啶并[2，3- g ]喹喔啉。标题化合物中的细胞毒性和抗病毒活性的基于细胞的测定中测试抗RNA病毒代表三个属的的黄病毒科家族，即BVDV（瘟病毒），YFV（黄病毒属）和HCV（丙型肝炎病毒属）。喹啉衍生物也针对含有单链，无论正义（单链RNA其他RNA病毒科的代表测试+）或负义（RNA - ，和双链基因组（双链RNA），以及针对两个代表） DNA病毒家族。尽管对CVB-5，Reo-1和RSV具有选择性活性，但一些喹啉类药物显示中等程度的活性。但是，属于所有类别的衍生物均显示出对BVDV的活性。最有效的是双三唑并喹啉1m，咪唑并喹啉2e和2h以及吡啶并喹喔啉4h，4j和5n（EC 50范围1-5μM）。当在复制子
• Synthesis of Two Novel Tricyclic Rings: Triazolo[4,5-g]quinolines and Pyrido[2,3-g]quinoxalines Derived from 6,7-Diaminoquinolines
  作者：Paolo Sanna、Antonio Carta、Giuseppe Paglietti

  DOI：10.3987/com-99-8766

  日期：——

  A general simple route for the synthesis of triazolo[4,5-g]quinolines and pyrido[2,3-g]quinoxalines is described. The heterocycles obtained were fully characterised by their spectroscopical properties. A revision of the nitration of the 2,3-dichloroacetanilide is also discussed, since it afforded the request nitro derivative to build up the key intermediate 6,7-diaminoquinolines.
• Synthesis, cytotoxicity and antiviral evaluation of new series of imidazo[4,5-g]quinoline and pyrido[2,3-g]quinoxalinone derivatives
  作者：Irene Briguglio、Roberta Loddo、Erik Laurini、Maurizio Fermeglia、Sandra Piras、Paola Corona、Paolo Giunchedi、Elisabetta Gavini、Giuseppina Sanna、Gabriele Giliberti、Cristina Ibba、Pamela Farci、Paolo La Colla、Sabrina Pricl、Antonio Carta

  DOI：10.1016/j.ejmech.2015.10.002

  日期：2015.11

  Linear aromatic N-tricyclic compounds with promising antiviral activity and minimal cytotoxicity were prepared and analyzed in the last years. Specifically, the pyrido[2,3-g]quinoxalinone nucleus was found endowed with high potency against several pathogenic RNA viruses as etiological agents of important veterinary and human pathologies. Following our research program on new antiviral agents we have designed, synthesized and assayed new series of imidazo[4,5-g]quinoline and pyrido[2,3-g]quinoxalinone derivatives. Lead compounds 1-4 were further modified to enhance their antiviral activity and reduce their cytotoxicity. Thus, different substituents were introduced on N atom at position 1 or the 0 atom at position 2 of the leads; contextually, several groups were inserted on the nitrogen atom at position 7 of diaminoquinoline intermediates. Title compounds were tested in cell-based assays for cytotoxicity and antiviral activity against RNA virus families containing single-stranded (either positive-sense (ssRNA+) or negative-sense (ssRNA-)), and double-stranded genomes (dsRNA), and against two representatives of DNA virus families. Some derivatives emerged as potential leads for further development as antiviral agents against some viruses of public health significance, such as RSV, Reo, BVDV and HCV. Particularly, compounds 4, 11b, 11c, 13c, 15a,18 and 21 resulted active against BVDV at concentrations ranging from 1.3 to 5 mu M. Compound 21 was also evaluated for its activity on the BVDV RdRp. Compound 4 was also tested as potential anti-HCV compound in a subgenomic replication assay. Molecular simulation results provided a molecular rationale for the anti-BVDV activity of these compounds. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, and preliminary in vitro and in silico antiviral activity of [4,7]phenantrolines and 1-oxo-1,4-dihydro-[4,7]phenantrolines against single-stranded positive-sense RNA genome viruses
  作者：Antonio Carta、Mario Loriga、Giuseppe Paglietti、Marco Ferrone、Maurizio Fermeglia、Sabrina Pricl、Tiziana Sanna、Cristina Ibba、Paolo La Colla、Roberta Loddo

  DOI：10.1016/j.bmc.2007.01.005

  日期：2007.3

  Following the antiviral screening of a wide series of new angular and linear N-tricyclic systems both in silico and in vitro, the [4,7]phenantroline nucleus emerged as a new ring system endowed with activity against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). Here, we report our new pathway to the synthesis of this nucleus and of several related derivatives, as well as the results of both cell-based antiviral assays and molecular dynamics simulations. In the antiviral screening, several compounds (9 and 16-20) showed to be fairly active against BVDV, CVB-2, and Polio I (EC50, 6-25 mu M). According to molecular dynamics simulations, compounds (15) and (17) emerged for its potency against the HCV NS5B, with a calculated IC50 of 11-12 mu M. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Substituted Aminoquinolines as Useful Intermediates for Preparation of Aromatic N-Tricyclic Systems
  作者：Antonio Carta、Michele Palomba、Paola Corona

  DOI：10.3987/com-06-10782

  日期：——

  An effective approach for the synthesis of new substituted mono and diaminoquinolines is described. Two known quinolines 7,8-dichloro-6-nitroquinoline (1) and 7,8-dichloro-6-nitrohydroquinolin-4-one (9) were used as key intermediates.

  描述了一种合成新的取代单和二氨基喹啉的有效方法。两种已知的喹啉 7,8-二氯-6-硝基喹啉 (1) 和 7,8-二氯-6-硝基氢喹啉-4-酮 (9) 被用作关键中间体。