4-chloro-8-methoxy-5-nitroquinoline | 145013-65-6

• 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: 4-chloro-8-methoxy-5-nitroquinoline
• CAS: 145013-65-6
• 化学式: C₁₀H₇ClN₂O₃
• 分子量: 238.63
• InChiKey: QEGSFOWDQSRVQO-UHFFFAOYSA-N

物化性质

• 熔点：
  191 °C
• 沸点：
  396.8±37.0 °C(Predicted)
• 密度：
  1.450±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  4-chloro-8-methoxy-5-nitroquinoline 在 四(三苯基膦)钯 、 氢溴酸 、 铁粉 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 苯 为溶剂， 反应 55.0h， 生成 6-bromo-8-methoxy-4-phenylquinoline-5-amine
  参考文献：
  名称：

  一条短途的新途径，可通往海洋来源的吡啶并r啶生物碱中的吡啶并[2,3,4- kl ] ac啶亚基

  摘要：

  吡咯并[2,3,4- kl ] ac啶环系统的一条短途新路线已经从容易获得的喹啉前体中开发出来，涉及两个关键步骤：（i）钯（0）​​催化的Suzuki交叉偶联反应是4-氯喹啉与芳基硼酸，和（ii）衍生自4-苯基-5-叠氮喹啉的腈的分子内腈插入反应。

  DOI：

  10.1039/c39920001453
• 作为产物：
  描述：

  2-氨基-4-硝基苯甲醚 在 五氯化磷 、 原甲酸三乙酯 、 三氯氧磷 作用下， 反应 8.0h， 生成 4-chloro-8-methoxy-5-nitroquinoline
  参考文献：
  名称：

  硝基双芳烃钯催化还原环化合成吡啶并吖啶生物碱

  摘要：

  开发了一种用于制备吡啶并[2,3,4- kl ]吖啶和吡啶并[4,3,2- kl ]吖啶生物碱的新方案。该方法的特点是使用 Mo(CO) 6作为还原剂进行远程钯催化的还原环化反应。包括三种硝基芳烃在内的各种底物都可以耐受，并以良好到极好的产率提供相应的产品。该方法已成功应用于去甲西哥林、苯乙烯胺C和necatorone骨架的全合成。

  DOI：

  10.1002/cjoc.202100094

文献信息

• The First Synthesis of the Pentacyclic Pyridoacridine Marine Alkaloids: Arnoamines A and B
  作者：Evelyne Delfourne、Celine Roubin、Jean Bastide

  DOI：10.1021/jo000011a

  日期：2000.9.1

  The synthesis of the marine pyridoacridine alkaloids arnoamines A and B has been accomplished in six and seven steps from 4-chloro-8-methoxy-5-nitroquinoline in 13% and 4% overall yield, respectively.

  从4-氯-8-甲氧基-5-硝基喹啉以六和七个步骤完成了海洋吡啶并r啶生物碱丙氨酸A和B的合成，总产率分别为13％和4％。
• 硝羟喹啉衍生物及其制备方法和用途
  申请人：江苏亚虹医药科技有限公司

  公开号：CN111960998A

  公开（公告）日：2020-11-20

  本发明公开了硝羟喹啉衍生物及其制备方法和用途。具体地，本发明公开了通式(I)所示的化合物、其制备方法、含有其的药物组合物，以及其在治疗感染性疾病或癌症中的用途。本发明的化合物具有异的抗肿瘤活性，可以被开发为治疗肿瘤的药物。通式(I)中各基团的定义与说明书中相同。
• Palladium-catalysed cross-coupling reactions of arylboronic acids with π-deficient heteroaryl chlorides
  作者：Naji M. Ali、Alexander McKillop、Michael B. Mitchell、Ricardo A. Rebelo、Philip J. Wallbank

  DOI：10.1016/s0040-4020(01)80481-6

  日期：1992.1

  The palladium-catalysed cross-coupling reactions of arylboronic acids with a variety of pi-deficient heteroaryl chlorides proceed in high yield. [1,4-Bis(diphenylphosphino)butane]palladium(II) dichloride was found to be a very satisfactory catalyst for monocyclic heteroaryl chlorides, whereas tetrakis(triphenylphosphine)palladium(O) was found to be excellent for a range of chloroquinoline derivatives.
• 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.
• Divergent Syntheses of Pyridoacridine Alkaloids <i>via</i> <scp>Palladium‐Catalyzed</scp> Reductive Cyclization with <scp>Nitro‐Biarenes</scp>
  作者：Bo Liu、Shuping Wang、Changhao Bian、Hongze Liao、Hou‐Wen Lin

  DOI：10.1002/cjoc.202100094

  日期：2021.7

  A divergent and novel protocol for the preparation of both pyrido[2,3,4-kl]acridine and pyrido[4,3,2-kl]acridine alkaloids was developed. This method featured the remote palladium-catalyzed reductive cyclization with Mo(CO)6 as reductant. A wide range of substrates including three types of nitro arenes were tolerated and afforded corresponding products in good to excellent yields. This method has been

  开发了一种用于制备吡啶并[2,3,4- kl ]吖啶和吡啶并[4,3,2- kl ]吖啶生物碱的新方案。该方法的特点是使用 Mo(CO) 6作为还原剂进行远程钯催化的还原环化反应。包括三种硝基芳烃在内的各种底物都可以耐受，并以良好到极好的产率提供相应的产品。该方法已成功应用于去甲西哥林、苯乙烯胺C和necatorone骨架的全合成。