N-<2-(3-hydroxyphenyl)ethyl>trifluoromethanesulfonamide | 119481-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-<2-(3-hydroxyphenyl)ethyl>trifluoromethanesulfonamide
• 英文别名: 1,1,1-trifluoro-N-[2-(3-hydroxyphenyl)ethyl]methanesulfonamide
• CAS: 119481-60-6
• 化学式: C₉H₁₀F₃NO₃S
• 分子量: 269.245
• InChiKey: ZJZHBVGCOVHASV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(氯甲基)喹啉 、 N-<2-(3-hydroxyphenyl)ethyl>trifluoromethanesulfonamide 在 potassium carbonate 、 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以13%的产率得到N-<2-<3-(2-quinolinylmethoxy)phenyl>ethyl>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
• 作为产物：
  描述：

  N-<2-(3-methoxyphenyl)ethyl>trifluoromethanesulfonamide 在 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以11.8 g (100%)的产率得到N-<2-(3-hydroxyphenyl)ethyl>trifluoromethanesulfonamide
  参考文献：
  名称：

  2-(phenoxymethyl)-quinazolines as antiallergic and antiinflammatory

  摘要：

  已披露的化合物的化学式为##STR1##其中##STR2##R.sup.2为氢、较低烷基、较低烷氧基、较低烷氧羰基、三氟甲基、硝基、氰基或卤素；R.sup.3为氢或较低烷基；R.sup.4为氢、较低烷基、--COOR.sup.3或##STR3##R.sup.5为较低烷基、单氟较低烷基、二氟较低烷基、多氟较低烷基、全氟较低烷基或##STR4##及其药用盐，以及它们在治疗白三烯介导的鼻支气管阻塞空气通道疾病，如过敏性鼻炎、过敏性支气管哮喘等，以及作为抗炎药物的用途。

  公开号：

  US04772703A1

文献信息

• 2-(phenoxymethyl)-quinazolines as antiallergic and antiinflammatory
  申请人：American Home Products Corporation

  公开号：US04772703A1

  公开（公告）日：1988-09-20

  There are disclosed compounds of the formula ##STR1## wherein ##STR2## R.sup.2 is hydrogen, loweralkyl, loweralkoxy, lower alkoxycarbonyl, trifluoromethyl, nitro, cyano or halo; R.sup.3 is hydrogen or loweralkyl; R.sup.4 is hydrogen, lower alkyl, --COOR.sup.3 or ##STR3## R.sup.5 is lower alkyl, monofluoroloweralkyl, difluoroloweralkyl, polyfluoroloweralkyl, perfluoroloweralkyl or ##STR4## 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 as antiinflammatory agents.

  已披露的化合物的化学式为##STR1##其中##STR2##R.sup.2为氢、较低烷基、较低烷氧基、较低烷氧羰基、三氟甲基、硝基、氰基或卤素；R.sup.3为氢或较低烷基；R.sup.4为氢、较低烷基、--COOR.sup.3或##STR3##R.sup.5为较低烷基、单氟较低烷基、二氟较低烷基、多氟较低烷基、全氟较低烷基或##STR4##及其药用盐，以及它们在治疗白三烯介导的鼻支气管阻塞空气通道疾病，如过敏性鼻炎、过敏性支气管哮喘等，以及作为抗炎药物的用途。
• Quinoline compounds as antiallergic and antiinflammatory agents
  申请人：American Home Products Corporation

  公开号：US04904786A1

  公开（公告）日：1990-02-27

  There are disclosed compounds of the formula ##STR1## wherein R.sup.1 is ##STR2## n is 0-5; R.sup.2 is hydrogen, loweralkyl, loweralkoxy, lower alkoxycarbonyl, trifluoromethyl, nitro, cyano or halo; R.sup.3 is hydrogen or loweralkyl; R.sup.4 hydrogen, lower alkyl, --COOR.sup.3 or ##STR3## R.sup.5 is lower alkyl, monofluoroloweralkyl, difluoroloweralkyl, polyfluoroloweralkyl, perfluoroloweralkyl or ##STR4## 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 as antiinflammatory agents.

  公开了以下化合物的结构式：##STR1## 其中 R.sup.1 是 ##STR2## n 为 0-5；R.sup.2 是氢、较低的烷基、较低的烷氧基、较低的烷氧羰基、三氟甲基、硝基、氰基或卤素；R.sup.3 是氢或较低的烷基；R.sup.4 是氢、较低的烷基、--COOR.sup.3 或 ##STR3## R.sup.5 是较低的烷基、单氟较低的烷基、二氟较低的烷基、多氟较低的烷基、全氟较低的烷基或 ##STR4## 及其药用盐，以及它们在治疗白三烯介导的鼻支气管阻塞的疾病条件，如过敏性鼻炎、过敏性支气管哮喘等，以及作为抗炎药的用途。
• MUSSER, JOHN H.;KUBRAK, DENNIS M.;KREFT, ANTHONY F. (III);BENDER, REINHOL+
  作者：MUSSER, JOHN H.、KUBRAK, DENNIS M.、KREFT, ANTHONY F. (III)、BENDER, REINHOL+

  DOI：——

  日期：——
• 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：——
• US4772703A
  申请人：——

  公开号：US4772703A

  公开（公告）日：1988-09-20