N-(4-(1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)phenyl)cyclopropanecarboxamide | 1312810-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(4-(1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)phenyl)cyclopropanecarboxamide
• 英文别名: N-[4-[1-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-5-oxo-1,2,4-triazol-4-yl]phenyl]cyclopropanecarboxamide
• CAS: 1312810-03-9
• 化学式: C₂₃H₂₁F₂N₇O₃
• 分子量: 481.462
• InChiKey: FUYZQRZEADPTAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,3-二氟苯 在 4-二甲氨基吡啶 、 aluminum (III) chloride 、 palladium 10% on activated carbon 、 氢气 、 十六烷基三甲基溴化铵 、 碳酸氢钠 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 30.0h， 生成 N-(4-(1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)phenyl)cyclopropanecarboxamide
  参考文献：
  名称：

  Design, synthesis and antifungal evaluation of 1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one

  摘要：

  Based on the structure of the active site of cytochrome P450 14 alpha-demethylase (CYP51) and the conclusions of the structure-activity relationships of azole antifungals, a series of 1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one of fluconazole analogs was synthesized. All compounds were characterized by IR, HRMS, (HNMR)-H-1 and C-13 NMR spectroscopic analysis. Results of preliminary antifungal in vitro test using eight human pathogenic species showed that some compounds displayed comparable or even better antifungal activities than reference drug fluconazole and that compound 3i exhibited significant activity against Candida albicans being worthy of further optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.001

文献信息

• Design, synthesis and antifungal evaluation of 1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one
  作者：Yongwei Jiang、Yongbin Cao、Jun Zhang、Yan Zou、Xiaoyun Chai、Honggang Hu、Qingjie Zhao、Qiuye Wu、Dazhi Zhang、Yuanying Jiang、Qingyan Sun

  DOI：10.1016/j.ejmech.2011.02.001

  日期：2011.7

  Based on the structure of the active site of cytochrome P450 14 alpha-demethylase (CYP51) and the conclusions of the structure-activity relationships of azole antifungals, a series of 1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one of fluconazole analogs was synthesized. All compounds were characterized by IR, HRMS, (HNMR)-H-1 and C-13 NMR spectroscopic analysis. Results of preliminary antifungal in vitro test using eight human pathogenic species showed that some compounds displayed comparable or even better antifungal activities than reference drug fluconazole and that compound 3i exhibited significant activity against Candida albicans being worthy of further optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.