1-methyl-4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]pyridinium iodide | 1085525-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]pyridinium iodide
• CAS: 1085525-56-9
• 化学式: C₁₆H₁₄F₃N₄O₂S*I
• 分子量: 510.278
• InChiKey: VDGJPFNPPMGAIJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.97
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  81.86
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-methyl-4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]pyridinium iodide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以90%的产率得到4-[5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis of new 4-[2-(4-methyl(amino)sulfonylphenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1,2,3,6-tetrahydropyridines: A search for novel nitric oxide donor anti-inflammatory agents

  摘要：

  A group of 4-[2-(4-methyl(amino) sulfonylphenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1,2,3,6-tetrahydropyridines (11-14) possessing a variety of substituents (Me, CO2Et, H, N = O) attached to the 1,2,3,6-tetrahydropyridyl N-1-nitrogen atom were synthesized and evaluated as anti-inflammatory agents. Structure-activity relationship data showed that the N-methyl-1,2,3,6-tetrahydropyridylmoiety is a suitable bioisosteric replacement for the tolyl moiety in celecoxib. The most potent compound 4-[5-(1-methyl- 1,2,3,6-tetrahydropyridin-4-yl)-3-trifluoromethylpyrazol-1-yl]benzenesulfonamide (11b; ED50 = 61.2 mg/kg po) exhibited an anti-inflammatory activity between that of the reference drugs celecoxib (ED50 = 10.8 mg/kg po) and aspirin (ED50 = 128.7 mg/kg po). The synthesis of model hybrid nitric oxide donor N-diazen-1-ium-1,2-diolate derivatives of 4-[2-(4-methyl(amino) sulfonylphenyl)-5-trifluoromethyl-2H- pyrazol-3-yl]-1,2,3,6-tetrahydropyridines (5) requires further investigation since the reaction of 1,2,3,6-tetrahydropyridines with nitric oxide furnished the undesired N-nitroso-1,2,3,6-tetrahydrohydropyridyl product rather than the desired N-diazen-1-ium-1,2-diolate-1,2,3,6-tetrahydropyridyl product. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.059
• 作为产物：
  描述：

  1-(4-氨基磺酰基苯基)-5-(吡啶-4-基)-3-三氟甲基-1H-吡唑 、 碘甲烷 以 丙酮 为溶剂， 反应 12.0h， 以93%的产率得到1-methyl-4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]pyridinium iodide
  参考文献：
  名称：

  Synthesis of new 4-[2-(4-methyl(amino)sulfonylphenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1,2,3,6-tetrahydropyridines: A search for novel nitric oxide donor anti-inflammatory agents

  摘要：

  A group of 4-[2-(4-methyl(amino) sulfonylphenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1,2,3,6-tetrahydropyridines (11-14) possessing a variety of substituents (Me, CO2Et, H, N = O) attached to the 1,2,3,6-tetrahydropyridyl N-1-nitrogen atom were synthesized and evaluated as anti-inflammatory agents. Structure-activity relationship data showed that the N-methyl-1,2,3,6-tetrahydropyridylmoiety is a suitable bioisosteric replacement for the tolyl moiety in celecoxib. The most potent compound 4-[5-(1-methyl- 1,2,3,6-tetrahydropyridin-4-yl)-3-trifluoromethylpyrazol-1-yl]benzenesulfonamide (11b; ED50 = 61.2 mg/kg po) exhibited an anti-inflammatory activity between that of the reference drugs celecoxib (ED50 = 10.8 mg/kg po) and aspirin (ED50 = 128.7 mg/kg po). The synthesis of model hybrid nitric oxide donor N-diazen-1-ium-1,2-diolate derivatives of 4-[2-(4-methyl(amino) sulfonylphenyl)-5-trifluoromethyl-2H- pyrazol-3-yl]-1,2,3,6-tetrahydropyridines (5) requires further investigation since the reaction of 1,2,3,6-tetrahydropyridines with nitric oxide furnished the undesired N-nitroso-1,2,3,6-tetrahydrohydropyridyl product rather than the desired N-diazen-1-ium-1,2-diolate-1,2,3,6-tetrahydropyridyl product. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.059