ethyl 2-((2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl) propyl)(3-phenoxypropyl)amino)acetate | 1354972-12-5

• 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: ethyl 2-((2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl) propyl)(3-phenoxypropyl)amino)acetate
• 英文别名: Ethyl 2-[[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-(3-phenoxypropyl)amino]acetate
• CAS: 1354972-12-5
• 化学式: C₂₄H₂₈F₂N₄O₄
• 分子量: 474.508
• InChiKey: AHVUCOMTQYRWML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-苯氧基溴丙烷 在 sodium azide 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 potassium iodide 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 33.0h， 生成 ethyl 2-((2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl) propyl)(3-phenoxypropyl)amino)acetate
  参考文献：
  名称：

  Design, synthesis and structure–activity relationships of new triazole derivatives containing N-substituted phenoxypropylamino side chains

  摘要：

  The incidence of invasive fungal infections and resistance to antifungal agents is increasing dramatically. It is highly desirable to develop novel azoles with improved biological profiles. The structure-activity relationship (SAR) of the N-substitutions was investigated in this study. In vitro antifungal activities revealed that sterically large groups were not favored for the N-substitutions. The removal of the N-substitutions had little effect on the antifungal activity. Two compounds with free amine group (i.e. 9a and 10a) showed excellent activity with broad antifungal spectrum. The SAR results were supported by molecular docking and the N-substitutions were found to be important for the conformation of the side chains. The SAR and binding mode of the azoles are useful for further lead optimization. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.013

文献信息

• Design, synthesis and structure–activity relationships of new triazole derivatives containing N-substituted phenoxypropylamino side chains
  作者：Shengzheng Wang、Gang Jin、Wenya Wang、Lingjian Zhu、Yongqiang Zhang、Guoqiang Dong、Yang Liu、Chunlin Zhuang、Zhenyuan Miao、Jianzhong Yao、Wannian Zhang、Chunquan Sheng

  DOI：10.1016/j.ejmech.2012.04.013

  日期：2012.7

  The incidence of invasive fungal infections and resistance to antifungal agents is increasing dramatically. It is highly desirable to develop novel azoles with improved biological profiles. The structure-activity relationship (SAR) of the N-substitutions was investigated in this study. In vitro antifungal activities revealed that sterically large groups were not favored for the N-substitutions. The removal of the N-substitutions had little effect on the antifungal activity. Two compounds with free amine group (i.e. 9a and 10a) showed excellent activity with broad antifungal spectrum. The SAR results were supported by molecular docking and the N-substitutions were found to be important for the conformation of the side chains. The SAR and binding mode of the azoles are useful for further lead optimization. (C) 2012 Elsevier Masson SAS. All rights reserved.