N-(3-chloro-4-fluoro-phenyl)-2-[[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-methyl-amino]acetamide | 1239174-65-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(3-chloro-4-fluoro-phenyl)-2-[[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-methyl-amino]acetamide
• 英文别名: N-(3-chloro-4-fluorophenyl)-2-[[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-methylamino]acetamide
• CAS: 1239174-65-2
• 化学式: C₂₀H₁₉ClF₃N₅O₂
• 分子量: 453.851
• InChiKey: CEUJJGZYVACYBM-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：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.3
• 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 aluminum (III) chloride 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 39.0h， 生成 N-(3-chloro-4-fluoro-phenyl)-2-[[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-methyl-amino]acetamide
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Antifungal Activity of New Triazole Derivatives

  摘要：

  A series of new antifungal triazole derivatives with phenylacetamide side chain were rational designed and synthesized on the basis of the structural information of lanosterol 14‐demethylase (CYP51). In vitro antifungal activity assay indicated that several compounds showed higher activity than fluconazole. Especially, compound 8h showed excellent inhibitory activity against Candida albicans and Cryptococcus neoformans (MIC = 0.0156 μg/mL), suggesting that it is a promising lead for the development of novel antifungal agents. The binding mode of compound 8h was investigated by flexible molecular docking. It interacted with CACYP51 through hydrophobic and van der Waals interactions.

  DOI：

  10.1111/j.1747-0285.2011.01138.x

文献信息

• Structure-Based Design, Synthesis, and Antifungal Activity of New Triazole Derivatives
  作者：Chunquan Sheng、Xiaoying Che、Wenya Wang、Shengzheng Wang、Yongbing Cao、Jianzhong Yao、Zhenyuan Miao、Wannian Zhang

  DOI：10.1111/j.1747-0285.2011.01138.x

  日期：2011.8

  A series of new antifungal triazole derivatives with phenylacetamide side chain were rational designed and synthesized on the basis of the structural information of lanosterol 14‐demethylase (CYP51). In vitro antifungal activity assay indicated that several compounds showed higher activity than fluconazole. Especially, compound 8h showed excellent inhibitory activity against Candida albicans and Cryptococcus neoformans (MIC = 0.0156 μg/mL), suggesting that it is a promising lead for the development of novel antifungal agents. The binding mode of compound 8h was investigated by flexible molecular docking. It interacted with CACYP51 through hydrophobic and van der Waals interactions.