methyl 2-fluoro-4-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)benzoate | 1538605-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: methyl 2-fluoro-4-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)benzoate
• 英文别名: Methyl 2-fluoro-4-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]benzoate
• CAS: 1538605-85-4
• 化学式: C₁₉H₁₈F₄N₂O₂
• 分子量: 382.358
• InChiKey: HBLAOULDCGKGCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-fluoro-4-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)benzoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 2-fluoro-4-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)benzoic 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：

  1-(3-三氟甲基苯基)哌嗪 、 2-氟-4-溴苯甲酸甲酯 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以88%的产率得到methyl 2-fluoro-4-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)benzoate
  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

文献信息

• Dibenzo[b,f][1,4]oxazepine derivatives as inhibitors of histone deacetylase
  申请人：Methylgene, Inc.

  公开号：EP2343286A1

  公开（公告）日：2011-07-13

  This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula (I) wherein (B), Q, J, L and Z are as defined in the specification.

  本发明涉及抑制组蛋白去乙酰化酶的化合物。更具体地说，本发明提供了式 (I) 的化合物，其中 (B)、Q、J、L 和 Z 如说明书中所定义。
• Inhibitors of histone deacetylase
  申请人：MethylGene Inc.

  公开号：EP2489657A2

  公开（公告）日：2012-08-22

  This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula (I) wherein (B), Q, J, L and Z are as defined in the specification.

  本发明涉及抑制组蛋白去乙酰化酶的化合物。更具体地说，本发明提供了式 (I) 的化合物，其中 (B)、Q、J、L 和 Z 如说明书中所定义。