4-isocyanato-2-(trifluoromethyl)-1,1'-biphenyl | 1324003-65-7

• 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: 4-isocyanato-2-(trifluoromethyl)-1,1'-biphenyl
• 英文别名: 4-Isocyanato-2-(trifluoromethyl)biphenyl；4-isocyanato-1-phenyl-2-(trifluoromethyl)benzene
• CAS: 1324003-65-7
• 化学式: C₁₄H₈F₃NO
• 分子量: 263.219
• InChiKey: DXHLULIPACFUAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-isocyanato-2-(trifluoromethyl)-1,1'-biphenyl 、 4-甲氧基烟酰胺 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.17h， 以8.1 g的产率得到4-甲氧基-n-(2-(三氟甲基)联苯-4-基氨基甲酰)烟酰胺
  参考文献：
  名称：

  4-Methoxy-N-[2-(trifluoromethyl)biphenyl-4-ylcarbamoyl]nicotinamide: A Potent and Selective Agonist of S1P₁

  摘要：

  The sphingosine-1-phosphate-1 receptor (S1P(1)) and its endogenous ligand sphingosine-1-phosphate (S1P) cooperatively regulate lymphocyte trafficking from the lymphatic system. Herein, we disclose 4-methoxy-N[2-(trifluoromethyl)biphenyl-4-ylcarbamoyl]nicotinamide (8), an uncommon example of a synthetic S1P(1) agonist lacking a polar headgroup, which is shown to effect dramatic reduction of circulating lymphocytes (POC = -78%) in rat 24 h after a single oral dose (1 mg/kg). The excellent potency that 8 exhibits toward S1P(1) (EC50 = 0.035 mu M, 96% efficacy) and the >100-fold selectivity that it displays against receptor subtypes S1P(2-5) suggest that it may serve as a valuable tool to understand the clinical relevance of selective S1P(1) agonism.

  DOI：

  10.1021/ml2001399
• 作为产物：
  描述：

  光气 、 2-(trifluoromethyl)biphenyl-4-amine 以 甲苯 为溶剂， 反应 3.0h， 生成 4-isocyanato-2-(trifluoromethyl)-1,1'-biphenyl
  参考文献：
  名称：

  4-Methoxy-N-[2-(trifluoromethyl)biphenyl-4-ylcarbamoyl]nicotinamide: A Potent and Selective Agonist of S1P₁

  摘要：

  The sphingosine-1-phosphate-1 receptor (S1P(1)) and its endogenous ligand sphingosine-1-phosphate (S1P) cooperatively regulate lymphocyte trafficking from the lymphatic system. Herein, we disclose 4-methoxy-N[2-(trifluoromethyl)biphenyl-4-ylcarbamoyl]nicotinamide (8), an uncommon example of a synthetic S1P(1) agonist lacking a polar headgroup, which is shown to effect dramatic reduction of circulating lymphocytes (POC = -78%) in rat 24 h after a single oral dose (1 mg/kg). The excellent potency that 8 exhibits toward S1P(1) (EC50 = 0.035 mu M, 96% efficacy) and the >100-fold selectivity that it displays against receptor subtypes S1P(2-5) suggest that it may serve as a valuable tool to understand the clinical relevance of selective S1P(1) agonism.

  DOI：

  10.1021/ml2001399