N-(4-(4-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]piperazin-1-yl)phenyl)dodecanamide | 1312759-95-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-(4-(4-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]piperazin-1-yl)phenyl)dodecanamide
• 英文别名: N-[4-[4-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]piperazin-1-yl]phenyl]dodecanamide
• CAS: 1312759-95-7
• 化学式: C₃₃H₄₆F₂N₆O₂
• 分子量: 596.764
• InChiKey: DFLVXZWFNWCDIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  86.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-(4-硝基苯基)哌嗪 在 4-二甲氨基吡啶 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 N-(4-(4-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]piperazin-1-yl)phenyl)dodecanamide
  参考文献：
  名称：

  Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives

  摘要：

  A series of novel 1,2,4-triazole derivatives with a 4-(4-substitutedphenyl) piperazine side chain were designed and synthesized based on the structure of lanosterol 14 alpha-demethylase (CYP51). Their antifungal activities against eight human pathogenic fungi were evaluated in vitro by measuring the minimal inhibitory concentrations. Nearly all tested compounds were found to be more potent against Candida albicans than control drug fluconazole. Noticeably, the MIC80 value of compounds 6,7,9,14 and 29 is 16 times lower than that of voriconazole against C. albicans. The activities of compounds 7 and 21 against Cryptococcus neoformans in vitro are comparable to that of voriconazole with a MIC80 value of 0.0156 mu g/mL. Moreover, the molecular model for the binding between compound 7 and the active site of CACYP51 was provided based on the computational docking results. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.042

文献信息

• Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives
  作者：Jianming Xu、Yongbing Cao、Jun Zhang、Shichong Yu、Yan Zou、Xiaoyun Chai、Qiuye Wu、Dazhi Zhang、Yuanying Jiang、Qingyan Sun

  DOI：10.1016/j.ejmech.2011.02.042

  日期：2011.7

  A series of novel 1,2,4-triazole derivatives with a 4-(4-substitutedphenyl) piperazine side chain were designed and synthesized based on the structure of lanosterol 14 alpha-demethylase (CYP51). Their antifungal activities against eight human pathogenic fungi were evaluated in vitro by measuring the minimal inhibitory concentrations. Nearly all tested compounds were found to be more potent against Candida albicans than control drug fluconazole. Noticeably, the MIC80 value of compounds 6,7,9,14 and 29 is 16 times lower than that of voriconazole against C. albicans. The activities of compounds 7 and 21 against Cryptococcus neoformans in vitro are comparable to that of voriconazole with a MIC80 value of 0.0156 mu g/mL. Moreover, the molecular model for the binding between compound 7 and the active site of CACYP51 was provided based on the computational docking results. (C) 2011 Elsevier Masson SAS. All rights reserved.