N-[3-[(2-quinolinyl)methoxy]phenyl]-1-butanesulfonamide | 111974-56-2

• 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-[3-[(2-quinolinyl)methoxy]phenyl]-1-butanesulfonamide
• 英文别名: N-[3-(quinolin-2-yl-methyloxy)phenyl]butanesulphonamide；N-[3-[(2-Quinolinyl)methoxy]phenyl]-1-butane sulfonamide；N-[3-(quinolin-2-ylmethoxy)phenyl]butane-1-sulfonamide
• CAS: 111974-56-2
• 化学式: C₂₀H₂₂N₂O₃S
• 分子量: 370.472
• InChiKey: GOSRRAUHGUCBIM-UHFFFAOYSA-N

物化性质

• 熔点：
  89-94 °C
• 沸点：
  538.6±60.0 °C(Predicted)
• 密度：
  1.270±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：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  间硝基苯酚 在 platinum(IV) oxide 氢气 、 caesium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 25.0 ℃ 、241.32 kPa 条件下， 反应 18.5h， 生成 N-[3-[(2-quinolinyl)methoxy]phenyl]-1-butanesulfonamide
  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

文献信息

• Heterocyclic sulphonamides
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0232954A2

  公开（公告）日：1987-08-19

  These are disclosed compounds of the formula wherein X is W is -O-, -S- when n = 0, or W is when n = 1, and the dotted line represents an optional double bond; Y is - CH2O - , - OCH2- , - CH2S, - SCH2- , n is 0 or 1; each R1 is independently hydrogen, lower alkyl, lower alkoxy, lower alkanoyl, halo, trifluoromethyl, cyano or nitro; RZ is hydrogen or lower alkyl; R3 is lower alkyl, perfluoroloweralkyl or perfluorophenyl, with the proviso that when n = 0, R3 is other than lower alkyl; each R4 is independently hydrogen or lower alkyl; and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like, and in antithrombotic therapy.

  这些化合物的公开式为 其中 X 是 W是-O-、-S- 当 n = 0 时，或 W 是 当 n = 1 时，虚线代表任选双键；Y 是 - CH2O - , - OCH2- , - CH2S, - SCH2- 、 n 是 0 或 1；每个 R1 独立地是氢、低级烷基、低级烷氧基、低级烷酰基、卤代、三氟甲基、氰基或硝基；RZ 是氢或低级烷基；R3 是低级烷基、全氟低级烷基或全氟苯基，但当 n = 0 时，R3 不是低级烷基；每个 R4 独立地为氢或低级烷基；及其药学上可接受的盐，以及它们在治疗白三烯介导的鼻支气管阻塞性气道疾病（如过敏性鼻炎、过敏性支气管哮喘等）和抗血栓治疗中的用途。
• 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。
• MUSSER, JOHN H.;KREFT, ANTHONY F.;BENDER, REINHOLD H. W.;KUBRAK, DENNIS M+, J. MED. CHEM., 32,(1989) N, C. 1176-1183
  作者：MUSSER, JOHN H.、KREFT, ANTHONY F.、BENDER, REINHOLD H. W.、KUBRAK, DENNIS M+

  DOI：——

  日期：——
• MOHRS, KLAUS;PERZBORN, ELISABETH;SEUTER, FRIEDEL;FRUCHTMANN, ROMANIS;KOHL+
  作者：MOHRS, KLAUS、PERZBORN, ELISABETH、SEUTER, FRIEDEL、FRUCHTMANN, ROMANIS、KOHL+

  DOI：——

  日期：——
• US4675405A
  申请人：——

  公开号：US4675405A

  公开（公告）日：1987-06-23