8-(3-nitrobenzyloxy)quinoline | 116253-66-8

• 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-(3-nitrobenzyloxy)quinoline
• 英文别名: [3-(8-Quinolyloxymethyl)phenyl]azinic acid；8-[(3-nitrophenyl)methoxy]quinoline
• CAS: 116253-66-8
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: JLIVIOKFJFUMRW-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  483.3±25.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(3-nitrobenzyloxy)quinoline 在 potassium tert-butylate 、 铁粉 、 氯化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-(3-((quinolin-8-yloxy)methyl)phenyl)acetamide
  参考文献：
  名称：

  Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)- N -phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors

  摘要：

  Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl) thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42 nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of alpha-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.04.010
• 作为产物：
  描述：

  8-羟基喹啉 生成 8-(3-nitrobenzyloxy)quinoline
  参考文献：
  名称：

  MOHRS, KLAUS;PERZBORN, ELISABETH;SEUTER, FRIEDEL;FRUCHTMANN, ROMANIS;KOHL+

  摘要：

  DOI：

文献信息

• Substituierte Phenylsulfonamide
  申请人：BAYER AG

  公开号：EP0261539A2

  公开（公告）日：1988-03-30

  Neue substituierte Phenylsulfonamide können durch Umsetzung von entsprechenden Aminen mit Sulfonhalogeniden hergestellt werden. Die neuen Verbindungen können als Wirkstoffe zur Hemmung von enzymatischen Reaktionen und zur Hemmung der Thrombozytenaggregationen eingesetzt werden.

  通过将相应的胺与磺酰卤反应，可以生成新的取代苯基磺酰胺。 新化合物可用作抑制酶反应和抑制血小板聚集的活性物质。
• Development of 8-benzyloxy-substituted quinoline ethers and evaluation of their antimicrobial activities
  作者：Po-Yee Chung、Roberto Gambari、Yi-Xin Chen、Chor-Hing Cheng、Zhao-Xiang Bian、Albert Sun-Chi Chan、Johnny Cheuk-On Tang、Polly Hang-Mei Leung、Chung-Hin Chui、Kim-Hung Lam

  DOI：10.1007/s00044-014-1217-4

  日期：2015.4

  A series of 8-benzyloxy-substituted quinoline ethers (2a-n) compounds were synthesized. All synthesized compounds were screened in vitro for their preliminary antimicrobial activities against two Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), two Gram-positive bacteria (Staphylococcus aureus and Staphylococcus epidermidis), and a fungal species (Aspergillus niger). Among all synthesized compounds, compound 2e showed a significant growth inhibitory activity with MIC value 3.125 mu g/mL which was comparable to 8-hydroxyquinoline (2.5 mu g/mL) and terbinafine (1.25 mu g/mL) against A. niger.
• US5093340A
  申请人：——

  公开号：US5093340A

  公开（公告）日：1992-03-03
• US5070096A
  申请人：——

  公开号：US5070096A

  公开（公告）日：1991-12-03
• US5202336A
  申请人：——

  公开号：US5202336A

  公开（公告）日：1993-04-13