2-(2-nitrophenoxymethyl)quinoline | 116253-72-6

• 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: 2-(2-nitrophenoxymethyl)quinoline
• 英文别名: 2-[(2-Nitrophenoxy)methyl]quinoline
• CAS: 116253-72-6
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: ZKUVNMDTDIRTAA-UHFFFAOYSA-N

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：
  0.06
• 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：

  2-(2-nitrophenoxymethyl)quinoline 在 platinum(IV) oxide 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， -70.0~10.0 ℃ 、241.32 kPa 条件下， 生成 1,1,1-trifluoro-N-[2-(quinolin-2-ylmethoxy)phenyl]methanesulfonamide
  参考文献：
  名称：

  N-[(Arylmethoxy)phenyl] and N-[(arylmethoxy)naphthyl] sulfonamides: potent orally active leukotriene d4 antagonists of novel structure

  摘要：

  Two series of compounds, N-[(arylmethoxy)phenyl] sulfonamides and N-[(arylmethoxy)naphthyl] sulfonamides, were prepared as leukotriene D4 (LTD4) antagonists. In the phenyl series, N-[3-(2-quinolinylmethoxy)phenyl]-trifluoromethanesulfonamide (Wy-48,252, 16) was the most potent inhibitor of LTD4-induced bronchoconstriction in the guinea pig. With an intragastric ID50 of 0.1 mg/kg (2-h pretreatment), 16 was 300 times more potent than LY-171,883. Compound 16 also intragastrically inhibited ovalbumin-induced bronchoconstriction in the guinea pig with an ID50 of 0.6 mg/kg. In vitro against LTD4-induced contraction of isolated guinea pig trachea pretreated with indomethacin and L-cysteine, 16 produced a pKB value of 7.7. In the rat PMN assay 16 inhibited both 5-lipoxygenase and cyclooxygenase (IC50's = 4.6 and 3.3 microM). In the naphthyl series, N-[7-(2-quinolinylmethoxy)-2-naphthyl]trifluoromethanesulfonamide (Wy-48,090, 47) in addition to potent LTD4 antagonist activity (on isolated guinea pig trachea 47 had a pKB value of 7.04) also had antiinflammatory activity (63% inhibition at 50 mg/kg in the rat carrageenan paw edema assay and 34% inhibition of TPA-induced inflammation at 1 mg/ear in the mouse ear edema model). Perhaps the antiinflammatory activity of 47 was due to its additional activity of inhibiting both 5-lipoxygenase and cyclooxygenase enzymes (IC50's = 0.23 and 11.9 microM, respectively, in rat PMN).

  DOI：

  10.1021/jm00126a006
• 作为产物：
  描述：

  2-喹啉基甲醇 生成 2-(2-nitrophenoxymethyl)quinoline
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Synthesis of [[(naphthalenylmethoxy)- and -(quinolinylmethoxy)phenyl]amino]oxoalkanoic acid esters. A novel series of leukotriene D4 antagonists and 5-lipoxygenase inhibitors
  作者：John H. Musser、Dennis M. Kubrak、Joseph Chang、Alan J. Lewis

  DOI：10.1021/jm00158a019

  日期：1986.8

  A series of novel [[(naphthalenylmethoxy)- and [[(quinolinylmethoxy)phenyl]amino]oxoalkanoic acid esters have been prepared. These compounds were tested as inhibitors of rat polymorphonuclear leukocyte (PMN) 5-lipoxygenase (LO) in vitro and as inhibitors of ovalbumin (OA) and leukotriene D4 (LTD4) induced bronchospasm in the guinea pig (GP) in vivo. Many naphthalenyl compounds were potent inhibitors

  已经制备了一系列新型的[[（（萘基甲氧基）-和[[（喹啉基甲氧基）苯基]氨基]氧代链烷酸酯。在体外测试了这些化合物作为大鼠多形核白细胞（PMN）5-脂氧合酶（LO）的抑制剂以及卵白蛋白（OA）和白三烯D4（LTD4）诱导的豚鼠（GP）支气管痉挛的抑制剂。GP中许多萘化合物是5-LO的有效抑制剂，而一些喹啉基化合物是LTD4介导的支气管痉挛的有效抑制剂。最有效的萘化合物4-[[[3-（2-萘甲氧基甲氧基）苯基]羟基氨基] -4-氧代丁酸甲酯（6v）在5-LO分析中的IC50为0.6 microM。体内最有效的化合物4-[[[3-（2-喹啉基甲氧基）苯基]羟基氨基] -4-氧代丁酸甲酯（6e）的ED50为3.3 mg / kg，为27。分别针对LTD4-和OA引起的支气管痉挛分别为4 mg / kg（十二指肠内）。当作为LTD4诱导的分离GP气管螺旋带收缩的拮抗剂进行测试时，显示6e是竞争性抑制剂，pKB值为5
• 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。
• MOHRS, KLAUS;PERZBORN, ELISABETH;SEUTER, FRIEDEL;FRUCHTMANN, ROMANIS;KOHL+
  作者：MOHRS, KLAUS、PERZBORN, ELISABETH、SEUTER, FRIEDEL、FRUCHTMANN, ROMANIS、KOHL+

  DOI：——

  日期：——
• 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