4-acetamino-5-nitro-2-(3-trifluoromethylphenyloxy)anisole | 98081-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-acetamino-5-nitro-2-(3-trifluoromethylphenyloxy)anisole
• 英文别名: N-[4-methoxy-2-nitro-5-[3-(trifluoromethyl)phenoxy]phenyl]acetamide
• CAS: 98081-50-6
• 化学式: C₁₆H₁₃F₃N₂O₅
• 分子量: 370.285
• InChiKey: MDOIAGZEKJUNNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  488.3±45.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-acetamino-5-nitro-2-(3-trifluoromethylphenyloxy)anisole 在 盐酸 、 磷酸 、 水 、 砷酸、原砷酸 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.33h， 生成 8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline
  参考文献：
  名称：

  WO2007/127930

  摘要：

  公开号：
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 溴 、 硝酸 作用下， 以 乙酸酐 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 4-acetamino-5-nitro-2-(3-trifluoromethylphenyloxy)anisole
  参考文献：
  名称：

  WO2007/127930

  摘要：

  公开号：

文献信息

• Compounds affecting gap junction activity
  申请人：Hua Duy H.

  公开号：US08809368B2

  公开（公告）日：2014-08-19

  This invention relates to novel quinoline compounds which affect gap junction activity. Also provided are methods of using such compounds and compositions containing the compounds to treat gap junction disorders.

  本发明涉及影响间隙连接活性的新奎奴啉化合物。还提供了使用这种化合物的方法和含有该化合物的组合物来治疗间隙连接障碍。
• COMPOUNDS AFFECTING GAP JUNCTION ACTIVITY
  申请人：HUA Duy H.

  公开号：US20090143425A1

  公开（公告）日：2009-06-04

  This invention relates to novel quinoline compounds which affect gap junction activity. Also provided are methods of using such compounds and compositions containing the compounds to treat gap junction disorders.

  本发明涉及新型喹啉化合物，其影响间隙连接活性。还提供了使用这种化合物的方法和含有这种化合物的组合物来治疗间隙连接障碍。
• Inhibition of human monoamine oxidase A and B by 5-phenoxy 8-aminoquinoline analogs
  作者：Narayan D. Chaurasiya、Shobana Ganesan、N.P. Dhammika Nanayakkara、Luiza R.S. Dias、Larry A. Walker、Babu L. Tekwani

  DOI：10.1016/j.bmcl.2011.12.108

  日期：2012.2

  8-Aminoquinolines (8-AQs) are important class of anti-infective therapeutics. 5-Phenoxy 8-aminoquinoline analogs have shown improved metabolic stability compared to primaquine. In view or predictive role of monoamine oxidases (MAO) in metabolism of 8-aminoquinolines the 5-phenoxy analogs were evaluated in vitro for the inhibition of recombinant human MAO-A and MAO-B. The analogs were several folds more potent inhibitors of MAO-A and MAO-B compared to primaquine, the parent drug, with selectivity for MAO-B. 5-(4-Trifluoromethylphenoxy)-4-methylprimaquine (6) Inhibited MAO-B with IC50 value of 150 nM (626-fold more potent than primaquine). These results will have important implications in optimizing metabolic stability of 8-AQs to improve therapeutic value and also indicate scope for development of 8-AQs as selective MAO inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and anti-breast cancer activities of substituted quinolines
  作者：Aibin Shi、Thu A. Nguyen、Srinivas K. Battina、Sandeep Rana、Dolores J. Takemoto、Peter K. Chiang、Duy H. Hua

  DOI：10.1016/j.bmcl.2008.04.024

  日期：2008.6

  Promising anti-breast cancer agents derived from substituted quinolines were discovered. The quinolines were readily synthesized in a large scale from a sequence of reactions starting from 4-acetamidoanisole. The Michael addition product was isolated as the reaction intermediate in the ring closing reaction of 4-amino-5-nitro-2-(3-trifluoromethylphenyloxy) anisole with methyl vinyl ketone leading to 6-methoxy-4-methyl-8-nitro-5-(3-trifluoromethylphenyloxy) quinoline (14). The amino function of 8-amino-6-methoxy-4- methyl-5-(3-trifluoromethylphenyloxy) quinoline, prepared from 14, was connected to various side chains via alkylation with N( 3-iodopropyl) phthalimide, Michael addition with acrylonitrile, and reductive amination with various heterocycle carboxaldehydes, such as imidazole-4-carboxaldehyde, thiophene-2-carboxaldehyde, and 2-furaldehyde. Effects of the substituted quinolines on cell viability of T47D breast cancer cells using trypan blue exclusion assay were examined. The results showed that the IC50 value of 6-methoxy-8-[(2-furanylmethyl) amino]-4-methyl-5-(3-trifluoromethylphenyloxy) quinoline is 16 +/- 3 nM, the lowest IC50 out of all the quinolines tested. IC50 values of three other quinolines are in the nanomolar range, a desirable range for pharmacological testing. (C) 2008 Elsevier Ltd. All rights reserved.
• US8809368B2
  申请人：——

  公开号：US8809368B2

  公开（公告）日：2014-08-19