Methyl 2-(2-acetyloxyethoxymethyl)-5-(4-pentylanilino)-1,2,4-triazole-3-carboxylate | 1258402-87-7

• 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 2-(2-acetyloxyethoxymethyl)-5-(4-pentylanilino)-1,2,4-triazole-3-carboxylate
• 英文别名: methyl 2-(2-acetyloxyethoxymethyl)-5-(4-pentylanilino)-1,2,4-triazole-3-carboxylate
• CAS: 1258402-87-7
• 化学式: C₂₀H₂₈N₄O₅
• 分子量: 404.466
• InChiKey: JIGRXNXYWBQBBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 2-(2-acetyloxyethoxymethyl)-5-(4-pentylanilino)-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2-(2-Hydroxyethoxymethyl)-5-(4-pentylanilino)-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 3-bromo-1-[(2-acetoxyethoxy)methyl]-1,2,4-triazole-5-carboxylate 、 4-正戊基苯胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以90%的产率得到Methyl 2-(2-acetyloxyethoxymethyl)-5-(4-pentylanilino)-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

文献信息

• Ligand-Mediated Highly Effective and Selective C−N Coupling for Synthesizing Bioactive<i>N</i>-Aryltriazole Acyclonucleosides
  作者：Yuting Fan、Yi Xia、Jingjie Tang、Palma Rocchi、Fanqi Qu、Juan Iovanna、Ling Peng

  DOI：10.1021/ol102537p

  日期：2010.12.17

  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.