1-(3,5-dimethyl-1-(2-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)-N-methylmethanamine | 1311146-71-0

• 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: 1-(3,5-dimethyl-1-(2-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)-N-methylmethanamine
• 英文别名: 1-[3,5-dimethyl-1-[[2-(trifluoromethyl)phenyl]methyl]pyrazol-4-yl]-N-methylmethanamine
• CAS: 1311146-71-0
• 化学式: C₁₅H₁₈F₃N₃
• 分子量: 297.323
• InChiKey: JTBMRIUXVROHQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((4-(三氟甲基)苯氧基)甲基)环氧乙烷 、 1-(3,5-dimethyl-1-(2-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)-N-methylmethanamine 以 乙醇 为溶剂， 以48%的产率得到1-(((3,5-dimethyl-1-(2-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)methyl)(methyl)amino)-3-(4-(trifluoromethyl)phenoxy)propan-2-ol
  参考文献：
  名称：

  Development of β-Amino Alcohol Derivatives That Inhibit Toll-like Receptor 4 Mediated Inflammatory Response as Potential Antiseptics

  摘要：

  Toll-like receptor 4 (TLR4) induced proinflammatory signaling has been directly implicated in severe sepsis and represents an attractive therapeutic target. Herein, we report our investigations into the structure-activity relationship and preliminary drug metabolism/pharmacokinetics study of beta-amino alcohol derivatives that inhibit the TLR4 signaling pathway. Lead compounds were identified from in vitro cellular examination with micromolar potency for their inhibitory effects on TLR4 signaling and subsequently assessed for their ability to suppress the TLR4-induced inflammatory response in an ex vivo whole blood model. In addition, the toxicology, specificity, solubility, brain-blood barrier permeability, and drug metabolism of several compounds were evaluated. Although further optimizations are needed, our findings lay the groundwork for the future drug development of this class of small molecule agents for the treatment of severe sepsis.

  DOI：

  10.1021/jm2003365
• 作为产物：
  描述：

  2-三氟甲基苄基氯 在 potassium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 1-(3,5-dimethyl-1-(2-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)-N-methylmethanamine
  参考文献：
  名称：

  Development of β-Amino Alcohol Derivatives That Inhibit Toll-like Receptor 4 Mediated Inflammatory Response as Potential Antiseptics

  摘要：

  Toll-like receptor 4 (TLR4) induced proinflammatory signaling has been directly implicated in severe sepsis and represents an attractive therapeutic target. Herein, we report our investigations into the structure-activity relationship and preliminary drug metabolism/pharmacokinetics study of beta-amino alcohol derivatives that inhibit the TLR4 signaling pathway. Lead compounds were identified from in vitro cellular examination with micromolar potency for their inhibitory effects on TLR4 signaling and subsequently assessed for their ability to suppress the TLR4-induced inflammatory response in an ex vivo whole blood model. In addition, the toxicology, specificity, solubility, brain-blood barrier permeability, and drug metabolism of several compounds were evaluated. Although further optimizations are needed, our findings lay the groundwork for the future drug development of this class of small molecule agents for the treatment of severe sepsis.

  DOI：

  10.1021/jm2003365