4-(4-aminophenyl)-1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one | 1312809-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-aminophenyl)-1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one
• 英文别名: 4-(4-Aminophenyl)-2-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-1,2,4-triazol-3-one
• CAS: 1312809-94-1
• 化学式: C₁₉H₁₇F₂N₇O₂
• 分子量: 413.386
• InChiKey: JIRAPVMWHBKLOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-异丙基苯甲酸 、 4-(4-aminophenyl)-1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 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)-4-isopropylbenzamide
  参考文献：
  名称：

  新型三唑衍生物作为抗真菌剂的合成，体外评价和分子对接研究

  摘要：

  根据来自白色念珠菌的羊毛甾醇14α-脱甲基酶（CACYP51）的活性位点，一系列1-（2-（2,4-二氟苯基）-2-羟基-3-（1 H -1,2,4）合成了-三唑-1-基）丙基）-1 H -1,2,4-三唑-5（4 H）-一衍生物作为氟康唑类似物。初步针对8种人类病原性真菌的抗真菌试验结果表明，这些化合物在一定程度上具有活性，并且一些化合物对白色念珠菌具有出色的抗真菌活性。比参考药物氟康唑。灵活的分子对接用于分析目标化合物的构效关系（SAR）。设计的化合物通过疏水，范德华力和氢键相互作用与CACYP51相互作用。

  DOI：

  10.1016/j.bmcl.2011.06.008
• 作为产物：
  描述：

  1,3-二氟苯 在 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 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 22.0h， 生成 4-(4-aminophenyl)-1-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-1,2,4-triazol-5(4H)-one
  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

• Synthesis, in vitro evaluation and molecular docking studies of new triazole derivatives as antifungal agents
  作者：Yongwei Jiang、Jun Zhang、Yongbing Cao、Xiaoyun Chai、Yan Zou、Qiuye Wu、Dazhi Zhang、Yuanying Jiang、Qingyan Sun

  DOI：10.1016/j.bmcl.2011.06.008

  日期：2011.8

  derivatives were synthesized as fluconazole analogs. Results of the preliminary antifungal tests against eight human pathogenic fungi in vitro showed that these compounds exhibited activities to some extent, and some displayed excellent antifungal activities against C. albicans than reference drug fluconazole. Flexible molecular docking was used to analyze the structure–activity relationships (SARs) of the

  根据来自白色念珠菌的羊毛甾醇14α-脱甲基酶（CACYP51）的活性位点，一系列1-（2-（2,4-二氟苯基）-2-羟基-3-（1 H -1,2,4）合成了-三唑-1-基）丙基）-1 H -1,2,4-三唑-5（4 H）-一衍生物作为氟康唑类似物。初步针对8种人类病原性真菌的抗真菌试验结果表明，这些化合物在一定程度上具有活性，并且一些化合物对白色念珠菌具有出色的抗真菌活性。比参考药物氟康唑。灵活的分子对接用于分析目标化合物的构效关系（SAR）。设计的化合物通过疏水，范德华力和氢键相互作用与CACYP51相互作用。
• 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.