2-methyl-6-hydroxy-8-nitroquinoline | 257892-16-3

• 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-methyl-6-hydroxy-8-nitroquinoline
• 英文别名: 2-methyl-8-nitroquinolin-6-ol
• CAS: 257892-16-3
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: NFQJCPSPWUFXPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-6-hydroxy-8-nitroquinoline 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 ethyl [(2-methyl-8-aminoquinolin-6-yloxy)acetate]
  参考文献：
  名称：

  Aqueous Coordination Chemistry of Quinoline-Based Fluorescence Probes for the Biological Chemistry of Zinc

  摘要：

  Metal-specific fluorescence probes are of increasing importance in understanding the neurobiology and general cell biology of zinc. Several quinoline-based compounds such as TSQ and zinquin have been employed to detect zinc in fluorescence microscopy experiments in vivo; however, the aqueous solution chemistry remains equivocal. In some cases, this family of probes is said to reveal labile pools of Zn(II) inside the cell, yet in other cases, these probes ate suggested to remove Zn(II) from tightly bound sites in proteins. Since the binding modes, coordination numbers, and thermodynamics of zinc-zinquin interactions in aqueous solution have not been established, these proposals are difficult to distinguish. Here we show that, under physiological conditions, the various forms of zinquin bind Zn(II) with a high degree of cooperativity forming 2:1 complexes. Potentiometric, UV-visible, and fluorescence methods all yield an overall binding constant of log K = 13.5 under physiological conditions. To put this number in perspective with other Zn chelators and biological ligands, we compare the calculated so-called pM values (-log[Zn(II)](free)) for a series of compounds with different stoichiometries under a typical condition. The pZn value for zinquin (9.3) is similar to that of EGTA. (9.5) but much smaller than the value for carbonic anhydrase (12.4) or EDTA (14.3) and, thus, serves as a useful gauge for comparing zinc affinities. With respect to in vivo applications of zinquin, such as intracellular fluorescence microscopy studies, we End that the typical detection limit for free Zn(II) in aqueous solution is 4 phl, or 0.3 parts per trillion, at pH 7.2. These results have implications for the availability of zinc in various intracellular compartments.

  DOI：

  10.1021/ja992709f
• 作为产物：
  描述：

  3-硝基-4-氨基苯酚 、 丁烯-2-醛 在 盐酸 、 磷酸 作用下， 反应 5.5h， 以40%的产率得到2-methyl-6-hydroxy-8-nitroquinoline
  参考文献：
  名称：

  N-杂环硝基芳基的可见光催化还原为抗坏血酸还原剂的苯胺

  摘要：

  已经开发出一种利用[Ru（bpy）3 ] 2+光催化剂，蓝光LED和抗坏血酸（AscH 2）的光还原方案，以将硝基N-杂芳基还原为相应的苯胺。根据实验和计算结果以及先前的研究，我们建议反应通过质子偶联的电子在AscH 2，光催化剂和硝基N-杂芳基之间转移而进行。该方法提供了一种绿色的催化程序，可以将例如4- / 8-硝基喹啉还原为相应的氨基喹啉，而后者是重要的抗疟疾药物中存在的亚结构。

  DOI：

  10.1021/acs.orglett.9b01205

文献信息

• Responsive Polymers-Based Dual Fluorescent Chemosensors for Zn²⁺Ions and Temperatures Working in Purely Aqueous Media
  作者：Tao Liu、Shiyong Liu

  DOI：10.1021/ac200095f

  日期：2011.4

  PEG-b-P(MEO2MA-co-ZQMA) micelles possess a slightly decreased detection limit for Zn2+ (∼14 nM), reversible binding between ZQMA moieties and Zn2+ ions at 37 °C can be achieved, as evidenced by the on/off switching of fluorescence emission via the sequential addition of Zn2+ and EDTA. In vitro fluorescence imaging studies suggested that the micelles can effectively enter into living cells and sensitively respond to

  我们报道了基于响应性双亲水嵌段共聚物（DHBCs）的Zn 2+离子和温度双荧光化学传感器的制备，并研究了热诱导胶束化和检测条件对Zn 2+离子探测灵敏度和结合可逆性的影响。首先合成了一种新型的基于喹啉的极性敏感型和Zn 2+识别型荧光单体（ZQMA，6）。明确定义的DHBC在热响应嵌段PEG- b -P（MEO 2 MA- co -OEGMA- co中带有喹啉基Zn 2+识别部分（ZQMA）-ZQMA）是通过在存在下通过2-（2-甲氧基乙氧基）甲基丙烯酸乙酯（MEO 2 MA），低聚乙二醇单甲基醚甲基丙烯酸甲酯（OEGMA）和ZQMA的可逆加成-断裂链转移（RAFT）聚合而合成的PEG的macroRAFT试剂的制备。热敏嵌段中的OEGMA含量在0-12.0 mol％的范围内变化，以调节其较低的临界溶液温度（LCST）。在20°C时，几乎无荧光的PEG- b - P（MEO 2 MA- co-
• Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
  作者：Aleksandar R. Todorov、Santeri Aikonen、Mikko Muuronen、Juho Helaja

  DOI：10.1021/acs.orglett.9b01205

  日期：2019.5.17

  A photoreductive protocol utilizing [Ru(bpy)3]2+ photocatalyst, blue light LEDs, and ascorbic acid (AscH2) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH2, photocatalyst, and the nitro N-heteroaryl. The method

  已经开发出一种利用[Ru（bpy）3 ] 2+光催化剂，蓝光LED和抗坏血酸（AscH 2）的光还原方案，以将硝基N-杂芳基还原为相应的苯胺。根据实验和计算结果以及先前的研究，我们建议反应通过质子偶联的电子在AscH 2，光催化剂和硝基N-杂芳基之间转移而进行。该方法提供了一种绿色的催化程序，可以将例如4- / 8-硝基喹啉还原为相应的氨基喹啉，而后者是重要的抗疟疾药物中存在的亚结构。
• Aqueous Coordination Chemistry of Quinoline-Based Fluorescence Probes for the Biological Chemistry of Zinc
  作者：Christoph J. Fahrni、Thomas V. O'Halloran

  DOI：10.1021/ja992709f

  日期：1999.12.1

  Metal-specific fluorescence probes are of increasing importance in understanding the neurobiology and general cell biology of zinc. Several quinoline-based compounds such as TSQ and zinquin have been employed to detect zinc in fluorescence microscopy experiments in vivo; however, the aqueous solution chemistry remains equivocal. In some cases, this family of probes is said to reveal labile pools of Zn(II) inside the cell, yet in other cases, these probes ate suggested to remove Zn(II) from tightly bound sites in proteins. Since the binding modes, coordination numbers, and thermodynamics of zinc-zinquin interactions in aqueous solution have not been established, these proposals are difficult to distinguish. Here we show that, under physiological conditions, the various forms of zinquin bind Zn(II) with a high degree of cooperativity forming 2:1 complexes. Potentiometric, UV-visible, and fluorescence methods all yield an overall binding constant of log K = 13.5 under physiological conditions. To put this number in perspective with other Zn chelators and biological ligands, we compare the calculated so-called pM values (-log[Zn(II)](free)) for a series of compounds with different stoichiometries under a typical condition. The pZn value for zinquin (9.3) is similar to that of EGTA. (9.5) but much smaller than the value for carbonic anhydrase (12.4) or EDTA (14.3) and, thus, serves as a useful gauge for comparing zinc affinities. With respect to in vivo applications of zinquin, such as intracellular fluorescence microscopy studies, we End that the typical detection limit for free Zn(II) in aqueous solution is 4 phl, or 0.3 parts per trillion, at pH 7.2. These results have implications for the availability of zinc in various intracellular compartments.