N'-[4-[5-[4-[[amino(pyridin-2-yl)methylidene]amino]-2-fluorophenyl]furan-2-yl]-3-propan-2-yloxyphenyl]pyridine-2-carboximidamide | 1413921-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: N'-[4-[5-[4-[[amino(pyridin-2-yl)methylidene]amino]-2-fluorophenyl]furan-2-yl]-3-propan-2-yloxyphenyl]pyridine-2-carboximidamide
• CAS: 1413921-10-4
• 化学式: C₃₁H₂₇FN₆O₂
• 分子量: 534.593
• InChiKey: RDQFVZWEMNGPFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲烷磺酸 、 N'-[4-[5-[4-[[amino(pyridin-2-yl)methylidene]amino]-2-fluorophenyl]furan-2-yl]-3-propan-2-yloxyphenyl]pyridine-2-carboximidamide 以 二氯甲烷 为溶剂， 反应 0.5h， 以0.56 g的产率得到2-[2-iso-propoxy-4-(2-pyridylimino)aminophenyl]-5-[2-fluoro-4-(2-pyridylimino)aminophenyl]furan methanesulfonate
  参考文献：
  名称：

  Antileishmanial bis-arylimidamides: DB766 analogs modified in the linker region and bis-arylimidamide structure–activity relationships

  摘要：

  Analogs of the lead antileishmanial bis-arylimidamide DB766 were prepared that possess unsymmetrical substitutions on the diphenylfuran linker, and an additional compound was synthesized that contains isopropoxy groups meta to the central furan. These agents all displayed nanomolar in vitro potency against intracellular Leishmania with selectivity indexes >100 compared to J774 macrophages. While the unsymmetrical analogs were toxic to mice when given ip at 30 mg/kg/day, the compound bearing the meta isopropoxy groups was well tolerated by mice and showed activity in a murine model of visceral leishmaniasis when administered ip at 30 mg/kg/day for five days. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.037
• 作为产物：
  描述：

  1-bromo-2-isopropoxy-4-nitrobenzene 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 10% Pd/C 、 氢气 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 20.0~100.0 ℃ 、344.75 kPa 条件下， 反应 48.0h， 生成 N'-[4-[5-[4-[[amino(pyridin-2-yl)methylidene]amino]-2-fluorophenyl]furan-2-yl]-3-propan-2-yloxyphenyl]pyridine-2-carboximidamide
  参考文献：
  名称：

  Antileishmanial bis-arylimidamides: DB766 analogs modified in the linker region and bis-arylimidamide structure–activity relationships

  摘要：

  Analogs of the lead antileishmanial bis-arylimidamide DB766 were prepared that possess unsymmetrical substitutions on the diphenylfuran linker, and an additional compound was synthesized that contains isopropoxy groups meta to the central furan. These agents all displayed nanomolar in vitro potency against intracellular Leishmania with selectivity indexes >100 compared to J774 macrophages. While the unsymmetrical analogs were toxic to mice when given ip at 30 mg/kg/day, the compound bearing the meta isopropoxy groups was well tolerated by mice and showed activity in a murine model of visceral leishmaniasis when administered ip at 30 mg/kg/day for five days. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.037