2-(5-nitro-biphenyl-2-yl)-benzofuran | 1166975-77-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(5-nitro-biphenyl-2-yl)-benzofuran
• 英文别名: 2-(4-Nitro-2-phenylphenyl)-1-benzofuran
• CAS: 1166975-77-4
• 化学式: C₂₀H₁₃NO₃
• 分子量: 315.328
• InChiKey: IYYFMWQENJDVGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-nitro-biphenyl-2-yl)-benzofuran 在 tin(II) chloride dihydrate 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 生成 C₂₀H₁₅NO
  参考文献：
  名称：

  Structurally Simple Inhibitors of Lanosterol 14α-Demethylase Are Efficacious In a Rodent Model of Acute Chagas Disease

  摘要：

  We report structure-activity studies of a large number of dialkyl imidazoles as inhibitors of Trypanosoma cruzi lanosterol-14 alpha-demethylase (L14DM). The compounds have a simple structure compared to posaconazole, another L14DM inhibitor that is an anti-Chagas drug candidate. Several compounds display potency for killing T cruzi amastigotes in vitro with values of EC50 in the 0.4-10 nM range. Two compounds were selected for efficacy studies in a mouse model of acute Chagas disease. At oral doses of 20-50 mg/kg given after establishment of parasite infection, the compounds reduced parasitemia in the blood to undetectable levels, and analysis of remaining parasites by PCR revealed a lack of parasites in the majority of animals. These dialkyl imidazoles are substantially less expensive to produce than posaconazole and are appropriate for further development toward an anti-Chagas disease clinical candidate.

  DOI：

  10.1021/jm900030h
• 作为产物：
  描述：

  2,3-苯并呋喃 、 2-phenyl-4-nitrobromobenzene 在 四(三苯基膦)钯 、 potassium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 2-(5-nitro-biphenyl-2-yl)-benzofuran
  参考文献：
  名称：

  Structurally Simple Inhibitors of Lanosterol 14α-Demethylase Are Efficacious In a Rodent Model of Acute Chagas Disease

  摘要：

  We report structure-activity studies of a large number of dialkyl imidazoles as inhibitors of Trypanosoma cruzi lanosterol-14 alpha-demethylase (L14DM). The compounds have a simple structure compared to posaconazole, another L14DM inhibitor that is an anti-Chagas drug candidate. Several compounds display potency for killing T cruzi amastigotes in vitro with values of EC50 in the 0.4-10 nM range. Two compounds were selected for efficacy studies in a mouse model of acute Chagas disease. At oral doses of 20-50 mg/kg given after establishment of parasite infection, the compounds reduced parasitemia in the blood to undetectable levels, and analysis of remaining parasites by PCR revealed a lack of parasites in the majority of animals. These dialkyl imidazoles are substantially less expensive to produce than posaconazole and are appropriate for further development toward an anti-Chagas disease clinical candidate.

  DOI：

  10.1021/jm900030h