4-(2,5-dimethylphenyl)-2-(3-(piperazin-1-yl)propyl)-2,4-dihydro-3H-1,2,4-triazol-3-one | 1346235-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2,5-dimethylphenyl)-2-(3-(piperazin-1-yl)propyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
• CAS: 1346235-43-5
• 化学式: C₁₇H₂₅N₅O
• 分子量: 315.418
• InChiKey: KIEBQUVYKHZAMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(2,5-dimethylphenyl)-2-(3-(piperazin-1-yl)propyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 、 1-[2-(2,4-difluorophenyl)-2,3-epoxypropyl]-1H-1,2,4-triazole methanesulfonate 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 1-(3-(4-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl) piperazin-1-yl)propyl)-4-(2,5-dimethylphenyl)-1H-1,2,4-triazol-5(4H)-one
  参考文献：
  名称：

  Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism

  摘要：

  The incidence of life-threatening fungal infections is increasing dramatically. In an attempt to develop novel antifungal agents, our previously synthesized phenoxyalkylpiperazine triazole derivatives were used as lead structures for further optimization. By means of structure-based bioisosterism, triazolone was used as a new bioisostere of oxygen atom. This type of bioisosteric replacement can improve the water solubility without loss of hydrogen-bonding interaction with the target enzyme. A series of triazolone-containing triazoles were rationally designed and synthesized. As compared with fluconazole, several compounds showed higher antifungal activity with broader spectrum, suggesting their potential for further evaluations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.019
• 作为产物：
  描述：

  4-(2,5-dimethylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4-(2,5-dimethylphenyl)-2-(3-(piperazin-1-yl)propyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism

  摘要：

  The incidence of life-threatening fungal infections is increasing dramatically. In an attempt to develop novel antifungal agents, our previously synthesized phenoxyalkylpiperazine triazole derivatives were used as lead structures for further optimization. By means of structure-based bioisosterism, triazolone was used as a new bioisostere of oxygen atom. This type of bioisosteric replacement can improve the water solubility without loss of hydrogen-bonding interaction with the target enzyme. A series of triazolone-containing triazoles were rationally designed and synthesized. As compared with fluconazole, several compounds showed higher antifungal activity with broader spectrum, suggesting their potential for further evaluations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.019