3-{[4-(3-aminophenoxy)butyl](methyl)amino}-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol | 1146681-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-{[4-(3-aminophenoxy)butyl](methyl)amino}-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol
• 英文别名: 1-[4-(3-Aminophenoxy)butyl-methyl-amino]-2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol；1-[4-(3-aminophenoxy)butyl-methylamino]-2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol
• CAS: 1146681-28-8
• 化学式: C₂₂H₂₇F₂N₅O₂
• 分子量: 431.485
• InChiKey: OUHIYTOGAIRJKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89.4
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-(2,4-difluorophenyl)-3-{methyl[4-(3-nitrophenoxy)butyl]amino}-1-(1H-1,2,4-triazol-1-yl)propan-2-ol 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 3-{[4-(3-aminophenoxy)butyl](methyl)amino}-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol
  参考文献：
  名称：

  Discovery of highly potent novel antifungal azoles by structure-based rational design

  摘要：

  On the basis of the active site of lanosterol 14 alpha-demethylase from Candida albicans (CACYP51), a series of new azoles were designed and synthesized. All the new azoles show excellent in vitro activity against most of the tested pathogenic fungi, which represent a class of promising leads for the development of novel antifungal agents. The MIC80 value of compounds 8c, 8i and 8n against C. albicans is 0.001 mu g/mL, indicating that these compounds are more potent than fluconazole, itraconazole and voriconazole. Flexible molecular docking was used to analyze the structure-activity relationships (SARs) of the compounds. The designed compounds interact with CACYP51 through hydrophobic, van der Waals and hydrogen-bonding interactions. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.07.144

文献信息

• Discovery of highly potent novel antifungal azoles by structure-based rational design
  作者：Wenya Wang、Chunquan Sheng、Xiaoying Che、Haitao Ji、Yongbing Cao、Zhenyuan Miao、Jianzhong Yao、Wannian Zhang

  DOI：10.1016/j.bmcl.2009.07.144

  日期：2009.10

  On the basis of the active site of lanosterol 14 alpha-demethylase from Candida albicans (CACYP51), a series of new azoles were designed and synthesized. All the new azoles show excellent in vitro activity against most of the tested pathogenic fungi, which represent a class of promising leads for the development of novel antifungal agents. The MIC80 value of compounds 8c, 8i and 8n against C. albicans is 0.001 mu g/mL, indicating that these compounds are more potent than fluconazole, itraconazole and voriconazole. Flexible molecular docking was used to analyze the structure-activity relationships (SARs) of the compounds. The designed compounds interact with CACYP51 through hydrophobic, van der Waals and hydrogen-bonding interactions. (C) 2009 Published by Elsevier Ltd.