N-(4-fluorophenyl)-2-(4-methylphenyl)imidazo[1,2-a]pyrazin-3-amine | 1286660-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(4-fluorophenyl)-2-(4-methylphenyl)imidazo[1,2-a]pyrazin-3-amine
• CAS: 1286660-56-7
• 化学式: C₁₉H₁₅FN₄
• mdl: MFCD27594458
• 分子量: 318.353
• InChiKey: DIWDIQAKBTYLQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-fluorophenyl)-2-(4-methylphenyl)imidazo[1,2-a]pyrazin-3-amine 在 palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 N-(4-fluorophenyl)-2-(4-methylphenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-amine
  参考文献：
  名称：

  Imidazolopiperazines: Hit to Lead Optimization of New Antimalarial Agents

  摘要：

  Starting from a hit series from a GNF compound library collection and based on a cell-based proliferation assay of Plasmodium falciparum, a novel imidazolopiperazine scaffold was optimized. SAR for this series of compounds is discussed, focusing on optimization of cellular potency against wild-type and drug resistant parasites and improvement of physiochemical and pharmacokinetic properties. The lead compounds in this series showed good potencies in vitro and decent oral exposure levels in vivo. In a Plasmodium berghei mouse infection model, one lead compound lowered the parasitemia level by 99.4% after administration of 100 mg/kg single oral dose and prolonged mice survival by an average of 17.0 days. The lead compounds were also well-tolerated in the preliminary in vitro toxicity studies and represents an interesting lead for drug development.

  DOI：

  10.1021/jm2003359
• 作为产物：
  描述：

  氨基吡嗪 、 4-氟苯基异氰酸酯 、 对甲基苯甲醛 在 高氯酸 作用下， 以 甲醇 为溶剂， 生成 N-(4-fluorophenyl)-2-(4-methylphenyl)imidazo[1,2-a]pyrazin-3-amine
  参考文献：
  名称：

  Imidazolopiperazines: Hit to Lead Optimization of New Antimalarial Agents

  摘要：

  Starting from a hit series from a GNF compound library collection and based on a cell-based proliferation assay of Plasmodium falciparum, a novel imidazolopiperazine scaffold was optimized. SAR for this series of compounds is discussed, focusing on optimization of cellular potency against wild-type and drug resistant parasites and improvement of physiochemical and pharmacokinetic properties. The lead compounds in this series showed good potencies in vitro and decent oral exposure levels in vivo. In a Plasmodium berghei mouse infection model, one lead compound lowered the parasitemia level by 99.4% after administration of 100 mg/kg single oral dose and prolonged mice survival by an average of 17.0 days. The lead compounds were also well-tolerated in the preliminary in vitro toxicity studies and represents an interesting lead for drug development.

  DOI：

  10.1021/jm2003359