1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)piperidin-4-one O-4-chlorobenzyl oxime | 1229313-55-6

• 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: 1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)piperidin-4-one O-4-chlorobenzyl oxime
• 英文别名: 1-[4-[(4-Chlorophenyl)methoxyimino]-1-piperidyl]-2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol；1-[4-[(4-chlorophenyl)methoxyimino]piperidin-1-yl]-2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol
• CAS: 1229313-55-6
• 化学式: C₂₃H₂₄ClF₂N₅O₂
• 分子量: 475.926
• InChiKey: FIMDKFOUSHCNPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-[(4-chlorophenyl)methoxy]piperidin-4-imine 、 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 5.0h， 生成 1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)piperidin-4-one O-4-chlorobenzyl oxime
  参考文献：
  名称：

  Structure-based rational design, synthesis and antifungal activity of oxime-containing azole derivatives

  摘要：

  In an attempt to find novel azole antifungal agents with improved activity and broader spectrum, computer modeling was used to design a series of new azoles with piperidin-4-one O-substituted oxime side chains. Molecular docking studies revealed that they formed hydrophobic and hydrogen-bonding interactions with lanosterol 14 alpha-demethylase of Candida albicans (CACYP51). In vitro antifungal assay indicates that most of the synthesized compounds showed good activity against tested fungal pathogens. In comparison with fluconazole, itraconazole and voriconazole, several compounds (such as 10c, 10e, and 10i) show more potent antifungal activity and broader spectrum, suggesting that they are promising leads for the development of novel antifungal agents. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.03.014

文献信息

• Structure-based rational design, synthesis and antifungal activity of oxime-containing azole derivatives
  作者：Yulan Xu、Chunquan Sheng、Wenya Wang、Xiaoying Che、Yongbing Cao、Guoqiang Dong、Shengzheng Wang、Haitao Ji、Zhenyuan Miao、Jianzhong Yao、Wannian Zhang

  DOI：10.1016/j.bmcl.2010.03.014

  日期：2010.5

  In an attempt to find novel azole antifungal agents with improved activity and broader spectrum, computer modeling was used to design a series of new azoles with piperidin-4-one O-substituted oxime side chains. Molecular docking studies revealed that they formed hydrophobic and hydrogen-bonding interactions with lanosterol 14 alpha-demethylase of Candida albicans (CACYP51). In vitro antifungal assay indicates that most of the synthesized compounds showed good activity against tested fungal pathogens. In comparison with fluconazole, itraconazole and voriconazole, several compounds (such as 10c, 10e, and 10i) show more potent antifungal activity and broader spectrum, suggesting that they are promising leads for the development of novel antifungal agents. (C) 2010 Published by Elsevier Ltd.