8-amino-5,7-dinitroquinoline | 31009-29-7

• 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-amino-5,7-dinitroquinoline
• 英文别名: 5,7-dinitro-[8]quinolylamine；5,7-Dinitro-[8]chinolylamin；5,7-Dinitro-8-amino-chinolin；5,7-dinitroquinolin-8-amine
• CAS: 31009-29-7
• 化学式: C₉H₆N₄O₄
• 分子量: 234.171
• InChiKey: PNNXRCCDLJTSRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-amino-5,7-dinitroquinoline 在 硫酸 、 sodium nitrite 作用下， 生成 5,7-dinitro-quinoline-8-diazo hydroxide
  参考文献：
  名称：

  Dikshoorn, Recueil des Travaux Chimiques des Pays-Bas, 1929, vol. 48, p. 552

  摘要：

  DOI：
• 作为产物：
  描述：

  5-硝基喹啉 在 potassium permanganate 、 硫酸 、 三氧化硫 、 氨 、 硝酸 作用下， 反应 30.5h， 生成 8-amino-5,7-dinitroquinoline
  参考文献：
  名称：

  .sigma.-Adduct formation between azines and liquid ammonia. 47. Frontier orbital interactions in the regioselectivity of the amination of nitroquinolines by liquid ammonia/potassium permanganate

  摘要：

  DOI：

  10.1021/jo00235a001

文献信息

• Synthesis of new polynuclear heterocyclic systems based on 7,8-diamino-5-nitroquinoline
  作者：A. M. Starosotnikov、M. A. Bastrakov

  DOI：10.1007/s11172-023-4082-9

  日期：2023.11

  Abstract A new method for the synthesis of 7,8-diamino-5-nitroquinoline, a convenient precursor of various polyheterocycles, was elaborated. The compound was further used in the synthesis of a number of pyrazine-, vic-triazole-, imidazole-, and selenadiazole-derived tricyclic heteroaromatic systems containing an annulated quinoline fragment.

  摘要 阐述了一种合成 7,8-二氨基-5-硝基喹啉（各种多杂环化合物的便捷前体）的新方法。该化合物进一步用于合成许多含有环状喹啉片段的吡嗪-、vic-三唑-、咪唑-和硒二唑衍生的三环杂芳族系统。
• Development of New Cathepsin B Inhibitors: Combining Bioisosteric Replacements and Structure-Based Design To Explore the Structure–Activity Relationships of Nitroxoline Derivatives
  作者：Izidor Sosič、Bojana Mirković、Katharina Arenz、Bogdan Štefane、Janko Kos、Stanislav Gobec

  DOI：10.1021/jm301544x

  日期：2013.1.24

  Human cathepsin B has many house-keeping functions, such as protein turnover in lysosomes. However, dysregulation of its activity is associated with numerous diseases, including cancers. We present here the structure-based design and synthesis of new cathepsin B inhibitors using the cocrystal structure of 5-nitro-8-hydroxyquinoline in the cathepsin B active site. A focused library of over 50 compounds was prepared by modifying positions 5, 7, and 8 of the parent compound nitroxoline. The kinetic parameters and modes of inhibition were characterized, and the selectivities of the most promising inhibitors were determined. The best performing inhibitor 17 was effective in cell-based in vitro models of tumor invasion, where it significantly abrogated invasion of MCF-10A neoT cells. These data show that we have successfully explored the structure-activity relationships of nitroxoline derivatives to provide new inhibitors that could eventually lead to compounds with clinical usefulness against the deleterious effects of cathepsin B in cancer progression.
• Kaufmann; Zeller, Chemische Berichte, 1917, vol. 50, p. 1630
  作者：Kaufmann、Zeller

  DOI：——

  日期：——
• Claus; Dewitz, Journal fur praktische Chemie (Leipzig 1954), 1896, vol. <2> 53, p. 538
  作者：Claus、Dewitz

  DOI：——

  日期：——
• Dikshoorn, Recueil des Travaux Chimiques des Pays-Bas, 1929, vol. 48, p. 552
  作者：Dikshoorn

  DOI：——

  日期：——