4-bromo-1-((4-fluorobenzyl)oxy)-2-(trifluoromethyl)benzene | 1538605-87-6

• 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: 4-bromo-1-((4-fluorobenzyl)oxy)-2-(trifluoromethyl)benzene
• CAS: 1538605-87-6
• 化学式: C₁₄H₉BrF₄O
• 分子量: 349.122
• InChiKey: PMWQRINVNGIBSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-羧基-3-氟苯硼酸 、 4-bromo-1-((4-fluorobenzyl)oxy)-2-(trifluoromethyl)benzene 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以30%的产率得到3-fluoro-4'-((4-fluorobenzyl)oxy)-3'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid
  参考文献：
  名称：

  R-Configuration of 4-Aminopyridyl-Based Inhibitors of CYP51 Confers Superior Efficacy Against Trypanosoma cruzi

  摘要：

  Sterol 14 alpha-demethylase (CYP51) is an important therapeutic target for fungal and parasitic infections due to its key role in the biosynthesis of ergosterol, an essential component of the cell membranes of these pathogenic organisms. We report the development of potent and selective D-tryptophan-derived inhibitors of T. cruzi CYP51. Structural information obtained from the cocrystal structure of CYP51 and (R)-2, which is >1000-fold more potent than its enantiomer (S)-1, was used to guide design of additional analogues. The in vitro efficacy data presented here for (R)-2 (R)-8, together with preliminary in vitro pharmacokinetic data suggest that this new CYP51 inhibitor scaffold series has potential to deliver drug candidates for treatment of T. cruzi infections.

  DOI：

  10.1021/ml500010m
• 作为产物：
  描述：

  4-溴-2-三氟甲基苯酚 、 4-氟溴苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以91%的产率得到4-bromo-1-((4-fluorobenzyl)oxy)-2-(trifluoromethyl)benzene
  参考文献：
  名称：

  R-Configuration of 4-Aminopyridyl-Based Inhibitors of CYP51 Confers Superior Efficacy Against Trypanosoma cruzi

  摘要：

  Sterol 14 alpha-demethylase (CYP51) is an important therapeutic target for fungal and parasitic infections due to its key role in the biosynthesis of ergosterol, an essential component of the cell membranes of these pathogenic organisms. We report the development of potent and selective D-tryptophan-derived inhibitors of T. cruzi CYP51. Structural information obtained from the cocrystal structure of CYP51 and (R)-2, which is >1000-fold more potent than its enantiomer (S)-1, was used to guide design of additional analogues. The in vitro efficacy data presented here for (R)-2 (R)-8, together with preliminary in vitro pharmacokinetic data suggest that this new CYP51 inhibitor scaffold series has potential to deliver drug candidates for treatment of T. cruzi infections.

  DOI：

  10.1021/ml500010m