8-羟基-2-甲基喹啉-5-(N,N-二甲基)磺酰胺 | 349543-92-6

• 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
• 中文名称: 8-羟基-2-甲基喹啉-5-(N,N-二甲基)磺酰胺
• 英文名称: 5-(N,N-dimethyl)sulfonamido-8-hydroxy-2-methylquinoline
• 英文别名: 8-hydroxy-2-methyl-5-N,N-dimethylaminosulfonylquinoline；8-hydroxy-2-methyl-quinoline-5-(N,N-dimetyl)sulfonamide；8-hydroxy-5-(N,N-dimethylsulfonamido)-2-methylquinoline；5-(N,N-dimethylsulfamoyl)-8-hydroxy-2-methylquinoline；5-N,N-dimethylaminosulfonyl-8-hydroxyquinaldine；8-hydroxyquinaldine-5-(N,N-dimethyl)sulfonamide；8-Hydroxy-N,N,2-trimethylquinoline-5-sulfonamide
• CAS: 349543-92-6
• 化学式: C₁₂H₁₄N₂O₃S
• 分子量: 266.321
• InChiKey: RGZRADKEZNIFNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-羟基-2-甲基喹啉-5-(N,N-二甲基)磺酰胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以96%的产率得到5-(N,N-dimethylaminosulfonyl)-7-bromo-8-hydroxyquinaldine
  参考文献：
  名称：

  Design and synthesis of 8-hydroxyquinoline-based radioprotective agents

  摘要：

  In radiation therapy, adverse side effects are often induced due to the excessive cell death that occurs in radiosensitive normal cells. The radiation-induced cell death of normal cells is caused, at least in part, by apoptosis, which undergoes via activation of p53 and increase in the p53 protein, a zinc-containing transcriptional factor, in response to cellular damage. Therefore, radioprotective drugs that can protect normal cells from radiation and thus suppress adverse side effects would be highly desirable. We report herein on the radioprotective activity of 8-hydroxyquinoline (8HQ) derivatives that were initially designed so as to interact with the Zn2+ in p53. Indeed, the 5,7-bis(methylaminosulfonyl)-8HQ and 8-methoxyquinoline derivatives considerably protected MOLT-4 cells against gamma-ray radiation (10 Gy), accompanied by a low cytotoxicity. However, mechanistic studies revealed that the interaction of these drugs with p53 is weak and the mechanism for inhibiting apoptosis appears to be different from that of previously reported radioprotectors such as bispicen, which inhibits apoptosis via the denaturation of p53 as well as by blocking both transcription-dependent and -independent apoptotic pathways. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.06.017
• 作为产物：
  描述：

  8-羟基喹哪啶 在 氯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 8-羟基-2-甲基喹啉-5-(N,N-二甲基)磺酰胺
  参考文献：
  名称：

  Synthesis of Oxovanadium Complexes and Their Apoptosis-Inducing Activity in Leukemia Cells

  摘要：

  不同配体的钒复合物被合成并评估对U937细胞的抗增殖活性。配体的烷基链长度影响抗增殖活性，其中两个复合物——3b和4——展现出强活性，IC50值分别为6.02和3.90 μM。Annexin V染色和DNA梯带形成表明这些复合物诱导了U937细胞的凋亡。

  DOI：

  10.1248/cpb.60.508

文献信息

• Photochemical Cleavage Reactions of 8-Quinolinyl Sulfonates in Aqueous Solution
  作者：Yoshiyuki Kageyama、Ryosuke Ohshima、Kazusa Sakurama、Yoshihisa Fujiwara、Yoshifumi Tanimoto、Yasuyuki Yamada、Shin Aoki

  DOI：10.1248/cpb.57.1257

  日期：——

  Photochemical cleavage reactions of 8-quinolinyl benzenesulfonate derivatives and related sulfonates in aqueous solutions are reported. The 8-quinolinyl benzenesulfonates undergo photolysis upon photoirradiation at 300-330 nm to give the corresponding 8-quinolinols and benzenesulfonic acids with the production of only negligible amounts of byproducts. The effects of substituent groups of the 8-quinolinyl

  报道了在水溶液中8-喹啉基苯磺酸盐衍生物和相关磺酸盐的光化学裂解反应。8-喹啉基苯磺酸盐在300-330 nm的光辐射下进行光解，得到相应的8-喹啉醇和苯磺酸，而副产物的生成量可忽略不计。研究了8-喹啉基部分和苯环的取代基对光解反应的影响。基于使用三重态敏化剂，三重态猝灭剂和电子供体的稳态机理研究，表明光解主要通过在激发的三重态下SO键的均相裂解而进行。
• Derivatives of 8-Hydroxy-2-methylquinoline Are Powerful Prototypes for Zinc Sensors in Biological Systems
  作者：Dierdre A. Pearce、Nathalie Jotterand、Isaac S. Carrico、Barbara Imperiali

  DOI：10.1021/ja0039839

  日期：2001.5.1

  The recent emphasis on understanding the myriad roles of zinc in both normal and diseased cells and tissues has placed an ever increasing demand on methods for sensitive and selective methods for real-time monitoring of free Zn^(2+) in complex biological samples. Chelation-enhanced fluorescent sensors for zinc, based on fluorophores such as quinoline, dansyl, fluorescein, and anthracene, have been

  最近对理解锌在正常和患病细胞和组织中的无数作用的重视已经对用于实时监测复杂生物样品中游离 Zn^(2+) 的灵敏和选择性方法提出了日益增长的需求。已经报道了基于诸如喹啉、丹磺酰、荧光素和蒽等荧光团的锌螯合增强荧光传感器。虽然这些试剂中的每一种都有独特的优势，但仍然存在灵敏度、选择性和特异性问题，这些问题可以通过易于合成操作的替代发色团来解决。在此，我们报告了 8-羟基-2-甲基喹啉 (Oxn) 单元的系统化学修饰，作为开发采用螯合增强荧光的新传感器的基础。特别是，
• Photochemical Cleavage Reaction of 8-Quinolinyl Sulfonates That Are Halogenated and Nitrated at the 7-Position
  作者：Shinya Ariyasu、Kengo Hanaya、Megumi Tsunoda、Masanori Kitamura、Masanori Hayase、Ryo Abe、Shin Aoki

  DOI：10.1248/cpb.59.1355

  日期：——

  Photochemical bond-cleavage reactions are potentially useful in chemistry, bioorganic chemistry and medicinal chemistry. We previously reported on a photochemical cleavage reaction of 8-quinolinyl sulfonate (8-QS) derivatives in aqueous solution at neutral pH, which we proposed to proceed via an excited triplet state. In this report, we report on the synthesis of some new photocleavable 8-QS derivatives

  光化学键断裂反应可能在化学，生物有机化学和药物化学中有用。我们先前曾报道过在中性pH下水溶液中的8-喹啉基磺酸盐（8-QS）衍生物发生光化学裂解反应，我们建议通过激发三重态进行。在本报告中，我们报告了一些新的可光裂解的8-QS衍生物的合成，其中在7位上引入了卤素原子或硝基，以试图改善光反应性并在其上产生红移。照射波长。溴和碘的引入可能导致光反应加速约1.5倍，这可能是由于重原子效应所致。还发现7-硝基-8-QS在> 360 nm处吸收，因此，
• Structural parameters of Zn(II) complexes of 8-hydroxyquinoline-based tripodal ligands affect fluorescence quantum yield
  作者：Maksim Royzen、James W. Canary

  DOI：10.1016/j.poly.2012.11.027

  日期：2013.7

  Tripodal ligands containing 8-hydroxyquinoline moieties have been reported with strong binding but perplexing fluorescence properties. Herein we describe the synthesis, photophysical properties and structural characterization of three 8-hydroxyquinoline-based fluorescent Zn(II) probes. Incorporation of the chromophore into a tripodal scaffold resulted in femtomolar sensitivity to the analyte. All three

  已经报道了含有8-羟基喹啉部分的三脚架配体具有强结合力但令人困惑的荧光性质。本文中，我们描述了三种基于8-羟基喹啉的荧光Zn（II）探针的合成，光物理性质和结构表征。将生色团结合到三脚架支架中导致对分析物的飞摩尔灵敏度。确定所有三个配体都以1：1的金属配体化学计量比结合Zn（II）。强大的锌亲和力被超过10倍的荧光灯开启所补充。X射线晶体学研究表明，锌配合物中的配体几何形状非常不同，这可能会影响其光谱行为。
• Design and synthesis of fluorescent activity probes for protein phosphatases
  作者：Garrett R. Casey、Jon R. Beck、Cliff I. Stains

  DOI：10.1016/bs.mie.2019.02.002

  日期：——

  Protein phosphatases act in concert with protein kinases to regulate and maintain the phosphoproteome. However, the catalog of chemical tools to directly monitor the enzymatic activity of phosphatases has lagged behind their kinase counterparts. In this chapter, we provide protocols for repurposing the phosphorylation-sensitive sulfonamido-oxine fluorophore known as Sox to afford direct activity probes

  蛋白质磷酸酶与蛋白质激酶协同作用，以调节和维持磷酸化蛋白质组。然而，直接监测磷酸酶的酶活性的化学工具目录已经落后于它们的激酶对应物。在本章中，我们提供了用于重新利用磷酸化敏感的磺酰氨基-氧肟荧光团（称为Sox）的方案，以提供磷酸酶的直接活性探针。使用经过验证的活性探针，可以使用重组酶进行抑制剂筛选，并且可以在未分级分离的细胞裂解物中研究磷酸酶在细胞信号传导中的作用。