Methyl 4-[4-ethoxy-3-[[[2-fluoro-4-(trifluoromethyl)benzoyl]amino]methyl]phenyl]-3-methylbenzoate | 1449754-43-1

• 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: Methyl 4-[4-ethoxy-3-[[[2-fluoro-4-(trifluoromethyl)benzoyl]amino]methyl]phenyl]-3-methylbenzoate
• 英文别名: methyl 4-[4-ethoxy-3-[[[2-fluoro-4-(trifluoromethyl)benzoyl]amino]methyl]phenyl]-3-methylbenzoate
• CAS: 1449754-43-1
• 化学式: C₂₆H₂₃F₄NO₄
• 分子量: 489.467
• InChiKey: IQQPNEUZFRKYIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 4-[4-ethoxy-3-[[[2-fluoro-4-(trifluoromethyl)benzoyl]amino]methyl]phenyl]-3-methylbenzoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 4-[4-ethoxy-3-({[2-fluoro-4-(trifluoromethyl)benzoyl]amino}methyl)phenyl]-3-methylbenzoic acid
  参考文献：
  名称：

  Peroxisome proliferator-activated receptor delta antagonists inhibit hepatitis C virus RNA replication

  摘要：

  It has been reported that ligand-mediated transcription factor peroxisome proliferator-activated receptor alpha (hPPAR alpha) is involved in hepatitis C virus (HCV) RNA replication, whereas hPPAR gamma is not, and the effect of hPPAR delta is unknown. Here, we show that hPPAR delta-selective antagonists effectively inhibit HCV RNA replication. We describe the design, synthesis and pharmacological evaluation of a series of biphenyl-4-carboxylic acid-type hPPAR delta antagonists, including previously reported compounds, as candidate anti-HCV agents. A representative compound (4c) dose-dependently inhibited HCV RNA replication (EC50 0.22 mu M), while exhibiting relatively weak cytotoxicity to the host cells (CC50 2.5 mu M). It also showed an additive and dose-dependent effect on the inhibition of HCV RNA replication by pegylated interferon alpha (Peg-IFN alpha) alone and by both Peg-IFN alpha and ribavirin (currently the clinical treatment of choice for HCV infection). Thus, combination of a hPPAR delta antagonist with current therapy may improve the efficacy of treatment for HCV infection. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.005
• 作为产物：
  描述：

  2-氟-4-(三氟甲基)苯甲酰胺 在 三乙基硅烷 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 53.0h， 生成 Methyl 4-[4-ethoxy-3-[[[2-fluoro-4-(trifluoromethyl)benzoyl]amino]methyl]phenyl]-3-methylbenzoate
  参考文献：
  名称：

  Peroxisome proliferator-activated receptor delta antagonists inhibit hepatitis C virus RNA replication

  摘要：

  It has been reported that ligand-mediated transcription factor peroxisome proliferator-activated receptor alpha (hPPAR alpha) is involved in hepatitis C virus (HCV) RNA replication, whereas hPPAR gamma is not, and the effect of hPPAR delta is unknown. Here, we show that hPPAR delta-selective antagonists effectively inhibit HCV RNA replication. We describe the design, synthesis and pharmacological evaluation of a series of biphenyl-4-carboxylic acid-type hPPAR delta antagonists, including previously reported compounds, as candidate anti-HCV agents. A representative compound (4c) dose-dependently inhibited HCV RNA replication (EC50 0.22 mu M), while exhibiting relatively weak cytotoxicity to the host cells (CC50 2.5 mu M). It also showed an additive and dose-dependent effect on the inhibition of HCV RNA replication by pegylated interferon alpha (Peg-IFN alpha) alone and by both Peg-IFN alpha and ribavirin (currently the clinical treatment of choice for HCV infection). Thus, combination of a hPPAR delta antagonist with current therapy may improve the efficacy of treatment for HCV infection. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.005