2-[2-甲基-8-[(4-甲基苯基)磺酰基氨基]喹啉-6-基]氧基乙酸 | 151606-29-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 2-[2-甲基-8-[(4-甲基苯基)磺酰基氨基]喹啉-6-基]氧基乙酸
• 英文名称: 2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxyacetic acid
• 英文别名: 2-methyl-8-p-toluenesulfonamido-6-quinolyloxyacetic acid；zinquin acid；zinquin；Zinquin A；2-[2-methyl-8-[(4-methylphenyl)sulfonylamino]quinolin-6-yl]oxyacetic acid
• CAS: 151606-29-0
• 化学式: C₁₉H₁₈N₂O₅S
• 分子量: 386.428
• InChiKey: CGNKOBNGEFZRQU-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114°C
• 沸点：
  608.0±65.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO
• 最大波长(λmax)：
  368 nm

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

制备方法与用途

Zinquin 是一种荧光传感器，用于观察活性锌离子。其激发波长 λ_ex = 364/385 nm。

反应信息

• 作为反应物：
  描述：

  溴甲基乙酸酯 、 2-[2-甲基-8-[(4-甲基苯基)磺酰基氨基]喹啉-6-基]氧基乙酸 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以91%的产率得到Zinquin AM ester
  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 2.75h， 生成 2-[2-甲基-8-[(4-甲基苯基)磺酰基氨基]喹啉-6-基]氧基乙酸
  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

• [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。
• Ionophores as cancer chemotherapeutic agents
  申请人：Lind E. Stuart

  公开号：US20060040980A1

  公开（公告）日：2006-02-23

  This invention relates to anti-cancer uses of ionophores of which clioquinol (5-chloro-7-iodo-8-hydroxyquinoline) is a prototype drug. The present invention is further directed toward using ionophores such as clioquinol alone, or in combination with metals (e.g., zinc or copper, manganese) as anti-cancer and anti-angiogenic agents. This invention further relates to the potentiation of the anti-cancer properties of polyunsaturated fatty acids when used in conjunction with the ionophores of the present invention. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing the ionophores of the present invention, and to methods of treating cancer as well as other disease states associated with unwanted angiogenesis and/or cellular proliferation, such as diabetic retinopathy, neovascular glaucoma, rheumatoid arthritis, and psoriasis, by administering effective amounts of such compounds.

  本发明涉及离子体的抗癌用途，其中氯喹啉（5-氯-7-碘-8-羟基喹啉）是一种原型药物。本发明的进一步方向是将离子体（如氯喹诺尔）单独使用，或与金属（如锌或铜、锰）结合使用，作为抗癌剂和抗血管生成剂。本发明还涉及多不饱和脂肪酸与本发明的离子团结合使用时可增强其抗癌特性。本发明还涉及含有本发明离子团的药物组合物的治疗或预防用途，以及通过施用有效量的此类化合物治疗癌症和其他与不希望的血管生成和/或细胞增殖有关的疾病状态（如糖尿病视网膜病变、新生血管性青光眼、类风湿性关节炎和牛皮癣）的方法。
• 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.
• 8-hydroxyquinoline compounds for treating a polyglutamine (polyQ)-expansion disease
  申请人：Massa Stephen

  公开号：US20070270462A1

  公开（公告）日：2007-11-22

  The present invention provides compositions and methods of treating a polyglutamine (poly Q) expansion disease in a subject using an 8-hydroxyquinoline compound.
• US7541467B2
  申请人：——

  公开号：US7541467B2

  公开（公告）日：2009-06-02