5-((4-butylphenyl)ethynyl)-1-((2-hydroxyethoxy)methyl)-1H-1,2,4-triazole-3-carboxamide | 1254971-20-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-((4-butylphenyl)ethynyl)-1-((2-hydroxyethoxy)methyl)-1H-1,2,4-triazole-3-carboxamide
• CAS: 1254971-20-4
• 化学式: C₁₈H₂₂N₄O₃
• 分子量: 342.398
• InChiKey: JIFKIAIZTROFEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 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：
  0.39
• 拓扑面积：
  103.26
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-((4-butylphenyl)ethynyl)-1-((2-hydroxyethoxy)methyl)-1H-1,2,4-triazole-3-carboxamide 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以50%的产率得到5-[5-(4-butylphenyl)-2H-triazol-4-yl]-1-(2-hydroxyethoxymethyl)-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  Bitriazolyl acyclonucleosides synthesized via Huisgen reaction using internal alkynes show antiviral activity against tobacco mosaic virus

  摘要：

  A family of novel bitriazolyl acyclonucleosides were synthesized using a simple and convenient one-step synthetic procedure via the Huisgen reaction by addition of NaN3 onto triazole nucleosides bearing internal alkynyl groups introduced at the 5-position of the triazole ring. Some of the compounds exhibited interesting antiviral activity against tobacco mosaic virus, demonstrating the importance of the bitriazolyl motif for the observed antiviral activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.141
• 作为产物：
  描述：

  5-bromo-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide 、 4-丁基苯乙炔 在 copper(l) iodide 、 四(三苯基膦)钯 、 lithium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.42h， 以90%的产率得到5-((4-butylphenyl)ethynyl)-1-((2-hydroxyethoxy)methyl)-1H-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  A novel arylethynyltriazole acyclonucleoside inhibits proliferation of drug-resistant pancreatic cancer cells

  摘要：

  Novel arylethynyltriazole acyclonucleosides were synthesized and assessed for their anticancer activity on drug-resistant pancreatic cancer MiaPaCa-2 cells. One lead compound was found to have much more potent apoptosis-related antiproliferative effects than gemcitabine, the current first-line treatment for pancreatic cancer. Further investigations showed that this active compound did not inhibit DNA synthesis, which means that it does not resemble gemcitabine and may involve a different mechanism of action. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.093