4-[2-(4-(methanesulfonyl)phenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-1-methyl-1,2,3,6-tetrahydropyridine | 1085525-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[2-(4-(methanesulfonyl)phenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-1-methyl-1,2,3,6-tetrahydropyridine
• 英文别名: 1-methyl-4-[2-(4-methylsulfonylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]-3,6-dihydro-2H-pyridine
• CAS: 1085525-57-0
• 化学式: C₁₇H₁₈F₃N₃O₂S
• 分子量: 385.41
• InChiKey: NISIBNYYXZEKDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[2-(4-(methanesulfonyl)phenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-1-methyl-1,2,3,6-tetrahydropyridine 、 氯甲酸乙酯 以 1,2-二氯乙烷 为溶剂， 以95%的产率得到4-[2-(4-(methanesulfonyl)phenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-1-(ethoxycarbonyl)-1,2,3,6-tetrahydropyridine
  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-methyl-4-[2-(4-(methanesulfonyl)phenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]pyridinium iodide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以99%的产率得到4-[2-(4-(methanesulfonyl)phenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-1-methyl-1,2,3,6-tetrahydropyridine
  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