2-methoxy-N-((4-(thiazol-2-yl)-3-(trifluoromethyl)phenyl)carbamoyl)benzamide | 1324003-71-5

• 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-methoxy-N-((4-(thiazol-2-yl)-3-(trifluoromethyl)phenyl)carbamoyl)benzamide
• 英文别名: 2-methoxy-N-[[4-(1,3-thiazol-2-yl)-3-(trifluoromethyl)phenyl]carbamoyl]benzamide
• CAS: 1324003-71-5
• 化学式: C₁₉H₁₄F₃N₃O₃S
• 分子量: 421.4
• InChiKey: ZEHHRWHPZDZDDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-三氟甲基-4-溴苯胺 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 72.5h， 生成 2-methoxy-N-((4-(thiazol-2-yl)-3-(trifluoromethyl)phenyl)carbamoyl)benzamide
  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

文献信息

• 4-Methoxy-<i>N</i>-[2-(trifluoromethyl)biphenyl-4-ylcarbamoyl]nicotinamide: A Potent and Selective Agonist of S1P₁
  作者：Lewis D. Pennington、Kelvin K. C. Sham、Alexander J. Pickrell、Paul E. Harrington、Michael J. Frohn、Brian A. Lanman、Anthony B. Reed、Michael D. Croghan、Matthew R. Lee、Han Xu、Michele McElvain、Yang Xu、Xuxia Zhang、Michael Fiorino、Michelle Horner、Henry G. Morrison、Heather A. Arnett、Christopher Fotsch、Min Wong、Victor J. Cee

  DOI：10.1021/ml2001399

  日期：2011.10.13

  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.