N-benzyl-5-nitroquinolin-8-amine | 332402-91-2

• 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: N-benzyl-5-nitroquinolin-8-amine
• CAS: 332402-91-2
• 化学式: C₁₆H₁₃N₃O₂
• mdl: MFCD00777817
• 分子量: 279.298
• InChiKey: VVLKQFFPLKRFDB-UHFFFAOYSA-N

物化性质

• 沸点：
  476.0±45.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-cyanomethoxyquinoline 在 硫酸 、 potassium nitrate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 N-benzyl-5-nitroquinolin-8-amine
  参考文献：
  名称：

  喹啉体系上的微波辅助亲核取代反应：硝基氧杂环丁烷氨基类似物的合成

  摘要：

  描述了一个可靠的协议，用于合成一系列药理学上令人关注的硝基氧杂环丁烷的5-氨基类似物（5-硝基-8-羟基喹啉）。O-氰基甲基化喹啉衍生物的氰基甲氧基被各种伯胺和仲胺空前取代，选择性地以中等至高收率提供了5-硝基喹啉-8-基胺。与常规加热相比，在微波条件下反应显着加速。

  DOI：

  10.1016/j.tetlet.2012.02.017

文献信息

• Regio- and Chemoselective Mono- and Bisnitration of 8-Amino quinoline Amides with Fe(NO₃)₃·9H₂O as Promoter and Nitro Source
  作者：Yan He、Ningning Zhao、Liqi Qiu、Xinying Zhang、Xuesen Fan

  DOI：10.1021/acs.orglett.6b02998

  日期：2016.12.2

  An efficient and regioselective remote C(5)–H nitration of 8-aminoquinoline amides by using the economical and nontoxic Fe(NO3)3·9H2O as promoter and nitro source has been developed. Furthermore, when CuCl2·2H2O was used as a catalyst, 8-aminoquinoline amides dominantly underwent bisnitration to give 5,7-dinitro-8-aminoquinoline amides. Notably, this is the first example in which Fe(NO3)3·9H2O plays

  通过使用经济，无毒的Fe（NO 3）3 ·9H 2 O作为促进剂和硝基源，开发了一种高效且区域选择性的8-氨基喹啉酰胺远程C（5）–H硝化方法。此外，当使用CuCl 2 ·2H 2 O作为催化剂时，主要将8-氨基喹啉酰胺进行双硝化以得到5,7-二硝基-8-氨基喹啉酰胺。值得注意的是，这是第一个例子，其中Fe（NO 3）3 ·9H 2 O既起螯合促进剂又起硝化剂的双重作用，而CuCl 2 ·2H 2 O则起喹啉双硝化的有效催化剂的作用。
• A microwave-assisted nucleophilic substitution reaction on a quinoline system: the synthesis of amino analogues of nitroxoline
  作者：Bogdan Štefane、Franc Požgan、Izidor Sosič、Stanislav Gobec

  DOI：10.1016/j.tetlet.2012.02.017

  日期：2012.4

  A reliable protocol for the synthesis of a series of 8-amino analogues of pharmacologically interesting nitroxoline (5-nitro-8-hydroxyquinoline) is described. The unprecedented displacement of the cyanomethoxy group of an O-cyanomethylated quinoline derivative by various primary and secondary amines selectively affords 5-nitroquinolin-8-ylamines in moderate-to-high yields. The reactions were accelerated

  描述了一个可靠的协议，用于合成一系列药理学上令人关注的硝基氧杂环丁烷的5-氨基类似物（5-硝基-8-羟基喹啉）。O-氰基甲基化喹啉衍生物的氰基甲氧基被各种伯胺和仲胺空前取代，选择性地以中等至高收率提供了5-硝基喹啉-8-基胺。与常规加热相比，在微波条件下反应显着加速。
• 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.