N-(2-(4-hydroxyphenoxy)phenyl)-N-methylmethanesulfonamide | 1301223-61-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-(4-hydroxyphenoxy)phenyl)-N-methylmethanesulfonamide
• 英文别名: N-[2-(4-hydroxyphenoxy)phenyl]-N-methylmethanesulfonamide
• CAS: 1301223-61-9
• 化学式: C₁₄H₁₅NO₄S
• 分子量: 293.343
• InChiKey: NZFPJQBFMKGKFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-(4-hydroxyphenoxy)phenyl)-N-methylmethanesulfonamide 、 N-(2-氯乙基)吡咯烷盐酸盐 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以86%的产率得到N-methyl-N-(2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenoxy)phenyl)methanesulfonamide
  参考文献：
  名称：

  Discovery of Dual Target Inhibitors against Cyclooxygenases and Leukotriene A₄ Hydrolyase

  摘要：

  Dual target inhibitors against COX-2. and LTA(4)H were designed by adding functional groups from a marketed COX-2 inhibitor, Nimesulide, to an existing LTA(4)H inhibitor 1-(2-(4-phenoxyphenoxy) ethyl) pyrrolidine. A series of phenoxyphenyl pyrrolidine compounds were synthesized and tested for their inhibition activities using enzyme assays and human whole blood assay. Introduction of small electron withdrawing groups like NO2 and CF3 in the ortho-position of the terminal phenyl ring was found to change the original single target LTA(4)H inhibitor to dual target LTA(4)H and COX-2 inhibitors. Compound 5a and 5m showed dual LTA(4)H and COX-2 inhibition activities in the enzyme assays and the I-EWE assay with IC50 values in the micromolar to submicromolar range. As their activities in HWB assay were comparable to the two starting single target inhibitors, the two compounds are promising for further studies. The strategy used in the current study may be generally applicable to other dual target drug designs.

  DOI：

  10.1021/jm200063s
• 作为产物：
  描述：

  N-(2-(4-methoxyphenoxy)phenyl)-N-methylmethanesulfonamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以81%的产率得到N-(2-(4-hydroxyphenoxy)phenyl)-N-methylmethanesulfonamide
  参考文献：
  名称：

  Discovery of Dual Target Inhibitors against Cyclooxygenases and Leukotriene A₄ Hydrolyase

  摘要：

  Dual target inhibitors against COX-2. and LTA(4)H were designed by adding functional groups from a marketed COX-2 inhibitor, Nimesulide, to an existing LTA(4)H inhibitor 1-(2-(4-phenoxyphenoxy) ethyl) pyrrolidine. A series of phenoxyphenyl pyrrolidine compounds were synthesized and tested for their inhibition activities using enzyme assays and human whole blood assay. Introduction of small electron withdrawing groups like NO2 and CF3 in the ortho-position of the terminal phenyl ring was found to change the original single target LTA(4)H inhibitor to dual target LTA(4)H and COX-2 inhibitors. Compound 5a and 5m showed dual LTA(4)H and COX-2 inhibition activities in the enzyme assays and the I-EWE assay with IC50 values in the micromolar to submicromolar range. As their activities in HWB assay were comparable to the two starting single target inhibitors, the two compounds are promising for further studies. The strategy used in the current study may be generally applicable to other dual target drug designs.

  DOI：

  10.1021/jm200063s