N-(2-phenoxy-3-pyridinyl)methanesulfonimide | 476453-77-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-phenoxy-3-pyridinyl)methanesulfonimide
• 英文别名: N-methylsulfonyl-N-(2-phenoxypyridin-3-yl)methanesulfonamide
• CAS: 476453-77-7
• 化学式: C₁₃H₁₄N₂O₅S₂
• 分子量: 342.397
• InChiKey: RAESNWMBICKTKB-UHFFFAOYSA-N

物化性质

• 沸点：
  495.9±55.0 °C(Predicted)
• 密度：
  1.467±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2-phenoxy-3-pyridinyl)methanesulfonimide 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 2.0h， 以91%的产率得到N-(2-phenoxypyridin-3-yl)methanesulfonamide
  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
• 作为产物：
  描述：

  2-phenoxy-3-nitropyridine 在 水 、 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 40.0h， 生成 N-(2-phenoxy-3-pyridinyl)methanesulfonimide
  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

• 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.