2-(3-fluoro-4-(N-(methylsulfonyl)acetamido)phenyl)-N-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide | 1071057-85-6

• 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: 2-(3-fluoro-4-(N-(methylsulfonyl)acetamido)phenyl)-N-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide
• 英文别名: 2-[4-[acetyl(methylsulfonyl)amino]-3-fluorophenyl]-N-[[2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl]methyl]propanamide
• CAS: 1071057-85-6
• 化学式: C₂₅H₃₀F₄N₄O₄S
• 分子量: 558.597
• InChiKey: NIYNUUZROSTMEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  ethyl 2-[3-fluoro-4-(methylsulfonylamino)phenyl]propionate 在 吡啶 、 lithium hydroxide monohydrate 、 1-羟基苯并三唑 、 1,2-二氯乙烷 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 2-(3-fluoro-4-(N-(methylsulfonyl)acetamido)phenyl)-N-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide
  参考文献：
  名称：

  Discovery of 2-(3,5-difluoro-4-methylsulfonaminophenyl)propanamides as potent TRPV1 antagonists

  摘要：

  A series of A-region analogues of 2-(3-fluoro-4-methylsufonamidophenyl)propanamide 1 were investigated as TRPV1 antagonists. The analysis of structure-activity relationship indicated that a fluoro group at the 3-(or/and) 5-position and a methylsulfonamido group at the 4-position were optimal for antagonism of TRPV1 activation by capsaicin. The most potent antagonist 6 not only exhibited potent antagonism of activation of hTRPV1 by capsaicin, low pH and elevated temperature but also displayed highly potent antagonism of activation of rTRPV1 by capsaicin. Further studies demonstrated that antagonist 6 blocked the hypothermic effect of capsaicin in vivo, consistent with its in vitro mechanism, and it showed promising analgesic activity in the formalin animal model.

  DOI：

  10.1016/j.bmcl.2018.05.043

文献信息

• Vanilloid receptor ligand compounds, pharmaceutical compositions containing them, a method of producing them and the use thereof to treat pain and various other conditions
  申请人：Frank Robert

  公开号：US20080269289A1

  公开（公告）日：2008-10-30

  Compounds corresponding to formula I: which act as vanilloid receptor ligands, pharmaceutical composition s containing such compounds, a method for producing the compounds, and the use of such compounds to treat pain and various other conditions.

  与公式I对应的化合物：作为辣椒素受体配体的化合物，含有这种化合物的药物组合物，制备这些化合物的方法，以及使用这些化合物治疗疼痛和其他各种疾病的用途。
• Vanilloid Receptor Ligand Compounds, Pharmaceutical Compositions Containing Them, a Method of Producing Them and the Use Thereof to Treat Pain and Various Other Conditions
  申请人：Frank Robert

  公开号：US20120302602A1

  公开（公告）日：2012-11-29

  Compounds corresponding to formula I: which act as vanilloid receptor ligands, pharmaceutical composition s containing such compounds, a method for producing the compounds, and the use of such compounds to treat pain and various other conditions.

  公式I对应的化合物：作为vanilloid受体配体的化合物，含有这些化合物的药物组合物，制备这些化合物的方法，以及使用这些化合物治疗疼痛和其他各种病症。
• VANILLOID-REZEPTOR LIGANDEN UND IHRE VERWENDUNG ZUR HERSTELLUNG VON ARZNEIMITTELN
  申请人：Grünenthal GmbH

  公开号：EP2146959A1

  公开（公告）日：2010-01-27
• US8252816B2
  申请人：——

  公开号：US8252816B2

  公开（公告）日：2012-08-28
• US8642623B2
  申请人：——

  公开号：US8642623B2

  公开（公告）日：2014-02-04