乙基2-(2-甲基-8-(4-甲基苯基磺酸基N乙酰胺基)喹啉-6-氧基)乙酸酯 | 181530-09-6

• 物质功能分类: 化学试剂 - 有机试剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙基2-(2-甲基-8-(4-甲基苯基磺酸基N乙酰胺基)喹啉-6-氧基)乙酸酯
• 英文名称: ethyl [(2-methyl-8-p-toluenesulfonylaminoquinolin-6-yloxy)acetate]
• 英文别名: zinquin ethyl ester；Zinquin ester；zinquin；ethyl 2-[2-methyl-8-[(4-methylphenyl)sulfonylamino]quinolin-6-yl]oxyacetate
• CAS: 181530-09-6
• 化学式: C₂₁H₂₂N₂O₅S
• 分子量: 414.482
• InChiKey: KCASTCXJTDRDFT-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114°C
• 沸点：
  578.0±60.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)
• 溶解度：
  溶于乙醇、甲醇、二甲基亚砜；微溶于水
• 最大波长(λmax)：
  364 nm

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙基2-(2-甲基-8-(4-甲基苯基磺酸基N乙酰胺基)喹啉-6-氧基)乙酸酯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.5h， 生成 [5-Bromo-2-methyl-8-(toluene-4-sulfonylamino)-quinolin-6-yloxy]-acetic acid
  参考文献：
  名称：

  Mahadevan, Indumathy B.; Kimber, Marc C.; Lincoln, Stephen F., Australian Journal of Chemistry, 1996, vol. 49, # 5, p. 561 - 568

  摘要：

  DOI：
• 作为产物：
  描述：

  8-amino-6-methoxy-2-methylquinoline 在 sodium hydroxide 、 三溴化硼 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.25h， 生成 乙基2-(2-甲基-8-(4-甲基苯基磺酸基N乙酰胺基)喹啉-6-氧基)乙酸酯
  参考文献：
  名称：

  Mahadevan, Indumathy B.; Kimber, Marc C.; Lincoln, Stephen F., Australian Journal of Chemistry, 1996, vol. 49, # 5, p. 561 - 568

  摘要：

  DOI：

文献信息

• Regioselective Introduction of Heteroatoms at the C-8 Position of Quinoline <i>N</i>-Oxides: Remote C–H Activation Using <i>N</i>-Oxide as a Stepping Stone
  作者：Heejun Hwang、Jinwoo Kim、Jisu Jeong、Sukbok Chang

  DOI：10.1021/ja5053768

  日期：2014.7.30

  Reported herein is the metal-catalyzed regioselective C-H functionalization of quinoline N-oxides at the 8-position: direct iodination and amidation were developed using rhodium and iridium catalytic systems, respectively. Mechanistic study of the amidation revealed that the unique regioselectivity is achieved through the smooth formation of N-oxide-chelated iridacycle and that an acid additive plays

  本文报道了金属催化的 8 位喹啉 N-氧化物的区域选择性 CH 官能化：分别使用铑和铱催化系统开发了直接碘化和酰胺化。酰胺化的机理研究表明，独特的区域选择性是通过 N-氧化物螯合的铱环的顺利形成实现的，并且酸添加剂在决定原脱金属的速率步骤中起着关键作用。虽然这种使用 N-氧化物作为导向基团的远程 CH 活化方法可以在温和条件下很容易地应用于各种杂环底物，具有高官能团耐受性，但证明了锌喹酯（一种荧光锌指示剂）的有效合成。
• [EN] NOVEL PREPARATION METHOD OF QUINOLINE N-OXIDE DERIVATIVE WITH AMIDE GROUP<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION D'UN DÉRIVÉ DE N-OXYDE DE QUINOLÉINE AYANT UN GROUPE AMIDE
  申请人：INST BASIC SCIENCE

  公开号：WO2015160125A1

  公开（公告）日：2015-10-22

  Provided are a preparation method of a quinoline N-oxide derivative with an amide group capable of easily introducing the amide group into the quinoline N-oxide derivative by simplified processes and mild reaction conditions, and a quinoline N-oxide derivative with an amide group prepared by using the same.

  提供了一种奎诺啉N-氧化物衍生物的制备方法，该方法能够通过简化的过程和温和的反应条件将酰胺基团轻松引入奎诺啉N-氧化物衍生物中，并且提供了使用该方法制备的带有酰胺基团的奎诺啉N-氧化物衍生物。
• 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.
• [EN] FLOW CYTOMETRY BASED ASSAY FOR BIOAVAILABLE ZINC<br/>[FR] ÉTUDE BASÉE SUR LA CYTOMÉTRIE DE FLUX POUR ZINC BIODISPONIBLE
  申请人：SHRINERS HOSPITALS CHILDREN

  公开号：WO2016164488A1

  公开（公告）日：2016-10-13

  Complexes and methods for detecting bioavailable zinc are provided. In particular, a zinc-binding complex can include a biotinylated zinc-binding protein and a polymeric microsphere. Methods can include contacting the zinc-binding complex with a sample, adding a fluorophore, and detecting and measuring a fluorescence signal emitted by the fluorophore. The methods can be used in a wide range of analytical assays.