2-(4-fluorophenyl)-6-nitroquinolin-4(1H)-one

• 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-fluorophenyl)-6-nitroquinolin-4(1H)-one
• 英文别名: 2-(4-fluorophenyl)-6-nitroquinolin-4-one；2-(4-Fluorophenyl)-6-nitroquinolin-4-OL；2-(4-fluorophenyl)-6-nitro-1H-quinolin-4-one
• 化学式: C₁₅H₉FN₂O₃
• 分子量: 284.246
• InChiKey: ZZGBBJNNYPCZPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-6-nitroquinolin-4(1H)-one 在 盐酸 、 sodium azide 、 乙醇 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 、 乙酸乙酯 为溶剂， 反应 34.0h， 生成 N6-[2-amino-6-(2-pyridyl)pyrimidin-4-yl]-2-(4-fluorophenyl)quinoline-4,6-diamine
  参考文献：
  名称：

  Quinolinyl Pyrimidines: Potent Inhibitors of NDH-2 as a Novel Class of Anti-TB Agents

  摘要：

  NDH-2 is an essential respiratory enzyme in Mycobacterium tuberculosis (Mtb), which plays an important role in the physiology of Mtb. Herein, we present a target-based effort to identify a new structural class of inhibitors for NDH-2. High-throughput screening of the AstraZeneca corporate collection resulted in the identification of quinolinyl pyrimidines as the most promising class of NDH-2 inhibitors. Structure-activity relationship studies showed improved enzyme inhibition (IC50) against the NDH-2 target, which in turn translated into cellular activity against Mtb. Thus, the compounds in this class show a good correlation between enzyme inhibition and cellular potency. Furthermore, early ADME profiling of the best compounds showed promising results and highlighted the quinolinyl pyrimidine class as a potential lead for further development.

  DOI：

  10.1021/ml300134b
• 作为产物：
  描述：

  4-氟苯甲酰乙酸乙酯 在 盐酸 、 Dowtherm A 作用下， 以 正丁醇 为溶剂， 反应 50.0h， 生成 2-(4-fluorophenyl)-6-nitroquinolin-4(1H)-one
  参考文献：
  名称：

  Quinolinyl Pyrimidines: Potent Inhibitors of NDH-2 as a Novel Class of Anti-TB Agents

  摘要：

  NDH-2 is an essential respiratory enzyme in Mycobacterium tuberculosis (Mtb), which plays an important role in the physiology of Mtb. Herein, we present a target-based effort to identify a new structural class of inhibitors for NDH-2. High-throughput screening of the AstraZeneca corporate collection resulted in the identification of quinolinyl pyrimidines as the most promising class of NDH-2 inhibitors. Structure-activity relationship studies showed improved enzyme inhibition (IC50) against the NDH-2 target, which in turn translated into cellular activity against Mtb. Thus, the compounds in this class show a good correlation between enzyme inhibition and cellular potency. Furthermore, early ADME profiling of the best compounds showed promising results and highlighted the quinolinyl pyrimidine class as a potential lead for further development.

  DOI：

  10.1021/ml300134b

文献信息

• One-Pot Allan-Robinson/Friedländer Route to Chromen-/Quinolin-4-ones through the Domino Acetylative Cyclisation of 2-Hydroxy-/2-Aminobenzaldehydes
  作者：Vijai K. Rai、Fooleswar Verma、Ganeshwar P. Sahu、Manorama Singh、Ankita Rai

  DOI：10.1002/ejoc.201701435

  日期：2018.1.31

  A domino reaction between 2‐hydroxy‐/2‐aminobenzaldehydes and α‐haloketones gives chromen‐4‐ones and quinolin‐4‐ones in good to excellent yields. This method represents a new extension of the Allan–Robinson and Friedländer reactions, and uses N‐heterocyclic‐carbene catalysis. This approach has the advantages of operational simplicity, ambient reaction conditions, and no by‐product formation.

  2-羟基/ 2-氨基苯甲醛与α-卤代酮之间的多米诺反应使chromen-4-ones和quinolin-4-ones的产率高到极好。该方法代表了Allan-Robinson和Friedländer反应的新扩展，并使用了N-杂环-卡宾催化。这种方法的优点是操作简单，环境反应条件好，并且不会形成副产物。
• Synthesis of 4-Quinolones via a Carbonylative Sonogashira Cross-Coupling Using Molybdenum Hexacarbonyl as a CO Source
  作者：Linda Åkerbladh、Patrik Nordeman、Matyas Wejdemar、Luke R. Odell、Mats Larhed

  DOI：10.1021/jo502400h

  日期：2015.2.6

  A palladium-catalyzed CO gas-free carbonylative Sonogashira/cyclization sequence for the preparation of functionalized 4-quinolones from 2-iodoanilines and alkynes via two different protocols is described. The first method (A) yields the cyclized products after only 20 min of microwave (MW) heating at 120 degrees C. The second method (B) is a gas-free one-pot two-step sequence which runs at room temperature, allowing the use of sensitive substituents (e.g., nitro and bromide groups). For both protocols, molybdenum hexacarbonyl was used as a solid source of CO.
• Quinolinyl Pyrimidines: Potent Inhibitors of NDH-2 as a Novel Class of Anti-TB Agents
  作者：Pravin S. Shirude、Beena Paul、Nilanjana Roy Choudhury、Chaitanya Kedari、Balachandra Bandodkar、Bheemarao G. Ugarkar

  DOI：10.1021/ml300134b

  日期：2012.9.13

  NDH-2 is an essential respiratory enzyme in Mycobacterium tuberculosis (Mtb), which plays an important role in the physiology of Mtb. Herein, we present a target-based effort to identify a new structural class of inhibitors for NDH-2. High-throughput screening of the AstraZeneca corporate collection resulted in the identification of quinolinyl pyrimidines as the most promising class of NDH-2 inhibitors. Structure-activity relationship studies showed improved enzyme inhibition (IC50) against the NDH-2 target, which in turn translated into cellular activity against Mtb. Thus, the compounds in this class show a good correlation between enzyme inhibition and cellular potency. Furthermore, early ADME profiling of the best compounds showed promising results and highlighted the quinolinyl pyrimidine class as a potential lead for further development.