5-(methylsulfonyl)quinolin-8-ol | 1417737-57-5

• 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: 5-(methylsulfonyl)quinolin-8-ol
• 英文别名: 5-Methylsulfonylquinolin-8-ol；5-methylsulfonylquinolin-8-ol
• CAS: 1417737-57-5
• 化学式: C₁₀H₉NO₃S
• 分子量: 223.252
• InChiKey: GJHAIKSCHCJHTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2,4-二甲氧基苯甲胺 、 5-(methylsulfonyl)quinolin-8-ol 以 乙醇 为溶剂， 反应 48.0h， 以15%的产率得到7-(((2,4-dimethoxybenzyl)amino)methyl)-5-(methylsulfonyl)quinolin-8-ol
  参考文献：
  名称：

  [EN] MDR-REVERSING 8-HYDROXY-QUINOLINE DERIVATIVES
  [FR] DÉRIVÉS DE 8-HYDROXY-QUINOLÉINE INVERSANT LA MULTIRÉSISTANCE AUX MÉDICAMENTS

  摘要：

  公开号：

  WO2017175018A3
• 作为产物：
  描述：

  3-氨基-4-羟苯基甲基砜 、 丙烯醛 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以57%的产率得到5-(methylsulfonyl)quinolin-8-ol
  参考文献：
  名称：

  Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases

  摘要：

  使用Betti反应高效生成2OG氧化酶抑制剂，包括KDM4去甲基酶。

  DOI：

  10.1039/c5cc06095h

文献信息

• MDR-reversing 8-hydroxy-quinoline derivatives
  申请人：MAGYAR TUDOMÁNYOS AKADÉMIA TERMÉSZETTUDOMÁNYI KUTATÓKÖZPONT

  公开号：US10744127B2

  公开（公告）日：2020-08-18

  The present invention is related to 8-hydroxy-quinoline derivatives having multidrug-resistance reversing activity with improved selectivity and increased cytotoxicity towards multidrug-resistant cancer cells, preparation thereof and use of the same in the treatment of cancer, especially multidrug-resistant variants thereof.

  本发明涉及具有多药耐药性逆转活性的 8-羟基喹啉衍生物，其选择性提高，对多药耐药性癌细胞的细胞毒性增强，本发明的制备方法及其在治疗癌症，特别是癌症的多药耐药性变体中的应用。
• 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.
• MDR-REVERSING 8-HYDROXY-QUINOLINE DERIVATIVES
  申请人：Magyar Tudományos Akadémia Természettudományi Kutatóközpont

  公开号：EP3440070A2

  公开（公告）日：2019-02-13
• Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases
  作者：C. C. Thinnes、A. Tumber、C. Yapp、G. Scozzafava、T. Yeh、M. C. Chan、T. A. Tran、K. Hsu、H. Tarhonskaya、L. J. Walport、S. E. Wilkins、E. D. Martinez、S. Müller、C. W. Pugh、P. J. Ratcliffe、P. E. Brennan、A. Kawamura、C. J. Schofield

  DOI：10.1039/c5cc06095h

  日期：——

  A Betti reaction was used for efficient generation of 2OG oxygenase inhibitors, including for KDM4 demethylases.

  使用Betti反应高效生成2OG氧化酶抑制剂，包括KDM4去甲基酶。
• [EN] MDR-REVERSING 8-HYDROXY-QUINOLINE DERIVATIVES<br/>[FR] DÉRIVÉS DE 8-HYDROXY-QUINOLÉINE INVERSANT LA MULTIRÉSISTANCE AUX MÉDICAMENTS
  申请人：MAGYAR TUDOMÁNYOS AKADÉMIA TERMÉSZETTUDOMÁNYI KUTATÓKÖZPONT

  公开号：WO2017175018A3

  公开（公告）日：2018-01-11