trans-2-(2,4-dichlorophenyl)-2,3-dihydro-3-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: trans-2-(2,4-dichlorophenyl)-2,3-dihydro-3-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one
• 英文别名: 2-(2,4-Dichlorophenyl)-3-(1,2,4-triazol-1-yl)chroman-4-one；2-(2,4-dichlorophenyl)-3-(1,2,4-triazol-1-yl)-2,3-dihydrochromen-4-one
• 化学式: C₁₇H₁₁Cl₂N₃O₂
• 分子量: 360.199
• InChiKey: QXWIALIVYQYEDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-2-(2,4-dichlorophenyl)-2,3-dihydro-3-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 68.0h， 以81%的产率得到trans-2-(2,4-dichlorophenyl)-2,3-dihydro-3-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one oxime
  参考文献：
  名称：

  Synthesis, in vitro antifungal activity and in silico study of 3-(1,2,4-triazol-1-yl)flavanones

  摘要：

  A series of novel 3-(1,2,4-triazol-1-yl)flavanones were synthesized based on the N-phenethylazole pharmacophore of azole antifungals. The results of antifungal assay revealed that 4'-fluoroflavanone derivative 4c exhibited the best profile of activity against Candida and Saccharomyces strains. Compound 4c was 4-16 times more potent than reference drug fluconazole against Candida albicans and Saccharomyces cerevisiae. The molecular docking study with lanosterol 14 alpha-demethylase, in silico toxicity risks and drug-likeness predictions were used to better define of title compounds as antifungal agents. The favorable drug-like property of compound 4c makes 3-(1,2,4-triazol-1-yl)flavanone prototype as a promising lead for the future development of azole antifungal agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.008
• 作为产物：
  描述：

  2-溴-2'-羟基苯乙酮 在 哌啶 、 盐酸 、 sodium nitrite 作用下， 以 水 、 异丙醇 为溶剂， 生成 trans-2-(2,4-dichlorophenyl)-2,3-dihydro-3-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis, in vitro antifungal activity and in silico study of 3-(1,2,4-triazol-1-yl)flavanones

  摘要：

  A series of novel 3-(1,2,4-triazol-1-yl)flavanones were synthesized based on the N-phenethylazole pharmacophore of azole antifungals. The results of antifungal assay revealed that 4'-fluoroflavanone derivative 4c exhibited the best profile of activity against Candida and Saccharomyces strains. Compound 4c was 4-16 times more potent than reference drug fluconazole against Candida albicans and Saccharomyces cerevisiae. The molecular docking study with lanosterol 14 alpha-demethylase, in silico toxicity risks and drug-likeness predictions were used to better define of title compounds as antifungal agents. The favorable drug-like property of compound 4c makes 3-(1,2,4-triazol-1-yl)flavanone prototype as a promising lead for the future development of azole antifungal agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.008