N-(3-phenoxy-4-pyridinyl)trifluoromethanesulfonamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3-phenoxy-4-pyridinyl)trifluoromethanesulfonamide
• 英文别名: 1,1,1-trifluoro-N-(3-phenoxypyridin-4-yl)methanesulfonamide
• 化学式: C₁₂H₉F₃N₂O₃S
• 分子量: 318.276
• InChiKey: CCVDPDRPPMKLTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  4-硝基-3-苯氧基吡啶N-氧化物 在 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 N-(3-phenoxy-4-pyridinyl)trifluoromethanesulfonamide
  参考文献：
  名称：

  Spectral and Crystallographic Study of Pyridinic Analogues of Nimesulide: Determination of the Active Form of Methanesulfonamides as COX-2 Selective Inhibitors

  摘要：

  Compound 7, N-(3-phenoxy-4-pyridinyl)trifluoromethanesulfonamide, showed in vitro (whole blood assay) a strong inhibitory activity on the two cyclooxygenase (COX) enzymes (IC50(COX-1) = 2.2 muM and IC50(COX-2) = 0.4 muM), being more active but less COX-2-selective than nimesulide. Physicochemical studies and structural analyses indicated that the anionic sulfonamidate species seemed to be the active form of methanesulfonamides, which optimally interacted with the COX enzymes' active sites.

  DOI：

  10.1021/jm020920n

文献信息

• Pyridinic sulfonamide derivatives method of production and use thereof
  申请人：Delarge Jacques

  公开号：US20050020642A1

  公开（公告）日：2005-01-27

  New pyridinic sulfonamide derivatives represented by a general formula (I), wherein R1, represents a mono- or polyhalogenated C1-12-alkyl or a mono- or poly-halogenated C3-8-cycloalkyl group. The method of production of such derivatives and their use as active therapeutic substance in the treatment of diseases such as inflammation, arthrosis, cancer, angiogenesis and asthma are also reported.

  新的吡啶磺酰胺衍生物由通式（I）表示，其中R1表示单卤化或多卤化的C1-12烷基或单卤化或多卤化的C3-8环烷基。还报告了这些衍生物的生产方法以及它们作为活性治疗物质治疗炎症、关节炎、癌症、血管生成和哮喘等疾病的用途。
• PYRIDINIC SULFONAMIDE DERIVATIVES, METHOD OF PRODUCTION AND USE THEREOF
  申请人：Université de Liège

  公开号：EP1432684B1

  公开（公告）日：2009-03-25
• US7226936B2
  申请人：——

  公开号：US7226936B2

  公开（公告）日：2007-06-05
• [EN] PYRIDINIC SULFONAMIDE DERIVATIVES, METHOD OF PRODUCTION AND USE THEREOF<br/>[FR] DERIVES DE SULFONAMIDE PYRIDINIQUE, PROCEDE DE FABRICATION ET D'UTILISATION
  申请人：UNIV LIEGE

  公开号：WO2003029217A2

  公开（公告）日：2003-04-10

  New pyridinic sulfonamide derivatives represented by a general formula (I), wherein R1, represents a mono- or polyhalogenated Cl-12-alkyl or a mono- or poly-halogenated C3-8-cycloalkyl group. The method of production of such derivatives and their use as active therapeutic substance in the treatment of diseases such as inflammation, arthrosis, cancer, angiogenesis and asthma are also reported.
• Spectral and Crystallographic Study of Pyridinic Analogues of Nimesulide: Determination of the Active Form of Methanesulfonamides as COX-2 Selective Inhibitors
  作者：Fabien Julémont、Xavier de Leval、Catherine Michaux、Jacques Damas、Caroline Charlier、François Durant、Bernard Pirotte、Jean-Michel Dogné

  DOI：10.1021/jm020920n

  日期：2002.11.1

  Compound 7, N-(3-phenoxy-4-pyridinyl)trifluoromethanesulfonamide, showed in vitro (whole blood assay) a strong inhibitory activity on the two cyclooxygenase (COX) enzymes (IC50(COX-1) = 2.2 muM and IC50(COX-2) = 0.4 muM), being more active but less COX-2-selective than nimesulide. Physicochemical studies and structural analyses indicated that the anionic sulfonamidate species seemed to be the active form of methanesulfonamides, which optimally interacted with the COX enzymes' active sites.