8-hydroxy-2-methylquinoline-5,7-disulfonyl chloride

• 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: 8-hydroxy-2-methylquinoline-5,7-disulfonyl chloride
• 英文别名: 8-hydroxy-2-methylquinoline-5,7-disulfonyl dichloride；2-Methyl-chinolinol-5,7-dichlorsulfonat
• 化学式: C₁₀H₇Cl₂NO₅S₂
• 分子量: 356.207
• InChiKey: DIHSCDRVBQLVJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-hydroxy-2-methylquinoline-5,7-disulfonyl chloride 在 氨 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以39%的产率得到
  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， 反应 2.0h， 生成 8-hydroxy-2-methylquinoline-5,7-disulfonyl chloride
  参考文献：
  名称：

  A cost-effective chitosan–oxine based thin film for a volatile acid vapour sensing application

  摘要：

  通过固定壳聚糖和氧昔，开发了一种基于聚合物薄膜的化学传感器，用于检测三氟乙酸蒸气。

  DOI：

  10.1039/d0nj01757d

文献信息

• 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，
• Design and synthesis of 8-hydroxyquinoline-based radioprotective agents
  作者：Shinya Ariyasu、Akiko Sawa、Akinori Morita、Kengo Hanaya、Misato Hoshi、Ippei Takahashi、Bing Wang、Shin Aoki

  DOI：10.1016/j.bmc.2014.06.017

  日期：2014.8

  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.
• A cost-effective chitosan–oxine based thin film for a volatile acid vapour sensing application
  作者：M. M. Akhil Kumar、V. M. Biju

  DOI：10.1039/d0nj01757d

  日期：——

  A polymer film based chemosensor was developed through the immobilization of chitosan and oxine, for the detection of TFA vapors.

  通过固定壳聚糖和氧昔，开发了一种基于聚合物薄膜的化学传感器，用于检测三氟乙酸蒸气。