methyl 1-((2-acetoxyethoxy)methyl)-5-((4-fluorophenyl)amino)-1H-1,2,4-triazole-3-carboxylate | 1258402-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 1-((2-acetoxyethoxy)methyl)-5-((4-fluorophenyl)amino)-1H-1,2,4-triazole-3-carboxylate
• CAS: 1258402-84-4
• 化学式: C₁₅H₁₇FN₄O₅
• 分子量: 352.322
• InChiKey: DKNADXFTJPBASB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104.57
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 1-((2-acetoxyethoxy)methyl)-5-((4-fluorophenyl)amino)-1H-1,2,4-triazole-3-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以96%的产率得到5-((4-fluorophenyl)amino)-1-((2-hydroxyethoxy)methyl)-1H-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  Ligand-Mediated Highly Effective and Selective C−N Coupling for Synthesizing BioactiveN-Aryltriazole Acyclonucleosides

  摘要：

  N-aryltriazole nucleosides are new chemical entities with potential biological activity. The two phosphor ligands, Synphos and Xantphos, had a selective and effective impact on Pd-catalyzed C-N coupling with the 5- and 3-bromotriazole acyclonucleoside isomers, affording the corresponding and otherwise difficult to achieve N-aryltriazole nucleosides with good to excellent yields. In addition, two of the synthesized nucleosides showed superior anticancer activity against drug-resistant pancreatic cancer, compared to the reference drug gemcitabine.

  DOI：

  10.1021/ol102537p
• 作为产物：
  描述：

  methyl 1-((2-acetoxyethoxy)methyl)-5-bromo-1H-1,2,4-triazole-3-carboxylate 、 4-氟苯胺 在 (S)-(-)-[(5,6),(5',6')-双(乙烯二氧)联苯-2,2'-基]二苯基磷 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以69%的产率得到methyl 1-((2-acetoxyethoxy)methyl)-5-((4-fluorophenyl)amino)-1H-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  Ligand-Mediated Highly Effective and Selective C−N Coupling for Synthesizing BioactiveN-Aryltriazole Acyclonucleosides

  摘要：

  N-aryltriazole nucleosides are new chemical entities with potential biological activity. The two phosphor ligands, Synphos and Xantphos, had a selective and effective impact on Pd-catalyzed C-N coupling with the 5- and 3-bromotriazole acyclonucleoside isomers, affording the corresponding and otherwise difficult to achieve N-aryltriazole nucleosides with good to excellent yields. In addition, two of the synthesized nucleosides showed superior anticancer activity against drug-resistant pancreatic cancer, compared to the reference drug gemcitabine.

  DOI：

  10.1021/ol102537p