5-硝基-8-(吡咯烷-1-基)喹啉 | 294194-84-6

• 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: 5-硝基-8-(吡咯烷-1-基)喹啉
• 英文名称: 5-nitro-8-pyrrolidin-1-yl-quinoline
• 英文别名: 5-Nitro-8-(pyrrolidin-1-yl)quinoline；5-nitro-8-pyrrolidin-1-ylquinoline
• CAS: 294194-84-6
• 化学式: C₁₃H₁₃N₃O₂
• mdl: MFCD00440055
• 分子量: 243.265
• InChiKey: DMERJCJHEOTUBG-UHFFFAOYSA-N

物化性质

• 沸点：
  452.0±35.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  62
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

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 2.25h， 生成 5-硝基-8-(吡咯烷-1-基)喹啉
  参考文献：
  名称：

  Development of New Cathepsin B Inhibitors: Combining Bioisosteric Replacements and Structure-Based Design To Explore the Structure–Activity Relationships of Nitroxoline Derivatives

  摘要：

  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.

  DOI：

  10.1021/jm301544x

文献信息

• 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。
• Androgen receptor modulators and methods of treating disease using the same
  申请人：Schlienger Nathalie

  公开号：US20070004679A1

  公开（公告）日：2007-01-04

  Disclosed herein are bicycloaryl compounds of Formula (I) that selectively modulate nuclear receptors, preferably the androgen receptor, or a pharmaceutically acceptable salt, ester, amide, or prodrug thereof, and methods of treating disease comprising administering a compound of Formula (I) to a patient in need thereof.

  本文公开了一种公式（I）的双环芳基化合物，其选择性调节核受体，优选为雄激素受体，或其药学上可接受的盐、酯、酰胺或前药，以及包括向需要治疗的患者给予公式（I）化合物的治疗疾病的方法。
• Androgen receptor modulators and method of treating disease using the same
  申请人：Schlienger Nathalie

  公开号：US20060014739A1

  公开（公告）日：2006-01-19

  Disclosed herein are bicycloaryl compounds of Formula (I) that selectively modulate nuclear receptors, preferably the androgen receptor, or a pharmaceutically acceptable salt, ester, amide, or prodrug thereof, and methods of treating disease comprising administering a compound of Formula (I) to a patient in need thereof.

  本文公开了式(I)的双环芳基化合物，其选择性调节核受体，优选为雄激素受体，或其药学上可接受的盐、酯、酰胺或前药，以及通过向需要治疗的患者施用式(I)化合物的方法治疗疾病。
• ANDROGEN RECEPTOR MODULATORS AND METHOD OF TREATING DISEASE USING THE SAME
  申请人：Schlienger Nathalie

  公开号：US20080009489A1

  公开（公告）日：2008-01-10

  Disclosed herein are bicycloaryl compounds of Formula (I) that selectively modulate nuclear receptors, preferably the androgen receptor, or a pharmaceutically acceptable salt, ester, amide, or prodrug thereof, and methods of treating disease comprising administering a compound of Formula (I) to a patient in need thereof.

  本文披露了公式(I)的双环芳基化合物，其有选择性地调节核受体，优选为雄激素受体，或其药学上可接受的盐、酯、酰胺或前药，以及治疗疾病的方法，包括向需要该化合物的患者施用公式(I)的化合物。
• US7268232B2
  申请人：——

  公开号：US7268232B2

  公开（公告）日：2007-09-11