N-<7-(2-quinolinylmethoxy)-2-naphthyl>trifluoromethanesulfonamide | 109485-96-3

• 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-<7-(2-quinolinylmethoxy)-2-naphthyl>trifluoromethanesulfonamide
• 英文别名: N-[7-(2-quinolinyl methoxy)-2-naphthalenyl]trifluoromethane sulfonamide；C,C,C-Trifluoro-N-[7-(quinolin-2-ylmethoxy)-naphthalen-2-yl]-methanesulfonamide；1,1,1-trifluoro-N-[7-(quinolin-2-ylmethoxy)naphthalen-2-yl]methanesulfonamide
• CAS: 109485-96-3
• 化学式: C₂₁H₁₅F₃N₂O₃S
• 分子量: 432.423
• InChiKey: VAXFCHHCDMSTSK-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  553.9±60.0 °C(Predicted)
• 密度：
  1.478±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-(氯甲基)喹啉 在 sodium methylate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 N-<7-(2-quinolinylmethoxy)-2-naphthyl>trifluoromethanesulfonamide
  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

• Quinolinyl (or pyridinyl) methoxy substituted naphthalene compounds as
  申请人：American Home Products Corporation

  公开号：US04661596A1

  公开（公告）日：1987-04-28

  There are disclosed compounds of the formula ##STR1## wherein X is --Ch.sub.2 CH.sub.2 --, --CH=CH--, ##STR2## Z is CR or N, when n=1; or Z is O, S, or NR, when n=0; R is hydrogen or loweralkyl; n is 0 or 1; R.sup.1 is hydroxy, amino, loweralkyl sulfonamido, perfluoro loweralkyl sulfonamido or OR; R.sup.2 is hydrogen or loweralkyl; R.sup.3 is hydrogen or loweralkyl; or R.sup.2 and R.sup.3 taken together form a benzene ring; and the dotted line represents an optional double bond; 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.

  已披露的化合物的结构式为##STR1##其中X为--Ch.sub.2 CH.sub.2 --，--CH=CH--，##STR2##Z为CR或N，当n=1时；或Z为O，S或NR，当n=0时；R为氢或低碳烷基；n为0或1；R.sup.1为羟基，氨基，低碳烷基磺酰胺基，全氟低碳烷基磺酰胺基或OR；R.sup.2为氢或低碳烷基；R.sup.3为氢或低碳烷基；或R.sup.2和R.sup.3一起形成苯环；虚线表示可选的双键；及其药用盐，以及它们在治疗白三烯介导的鼻支气管阻塞气道疾病，如过敏性鼻炎，过敏性支气管哮喘等方面的用途。
• 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：——
• KREFT, ANTHONY F. , II;MUSSER, JOHN H.;PARTISON, THOMAS W.;YARDLEY, JOHN +
  作者：KREFT, ANTHONY F. , II、MUSSER, JOHN H.、PARTISON, THOMAS W.、YARDLEY, JOHN +

  DOI：——

  日期：——
• KREFT, ANTHONU F.;MUSSER, JOHN H.;PATTISON, THOMAS W.;YARDLEY, JOHN P.
  作者：KREFT, ANTHONU F.、MUSSER, JOHN H.、PATTISON, THOMAS W.、YARDLEY, JOHN P.

  DOI：——

  日期：——
• US4661596A
  申请人：——

  公开号：US4661596A

  公开（公告）日：1987-04-28