1-(3,4-dihydro-3-m-tolyl-2-(1H-1,2,4-triazol-1-yl)quinazolin-4-yl)-3,3-dimethylbutan-2-one | 1422541-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-(3,4-dihydro-3-m-tolyl-2-(1H-1,2,4-triazol-1-yl)quinazolin-4-yl)-3,3-dimethylbutan-2-one
• 英文别名: 3,3-dimethyl-1-[3-(3-methylphenyl)-2-(1,2,4-triazol-1-yl)-4H-quinazolin-4-yl]butan-2-one
• CAS: 1422541-95-4
• 化学式: C₂₃H₂₅N₅O
• 分子量: 387.484
• InChiKey: VSYIKTIAAVDIJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[2-(triphenylphosphoranylideneamino)phenyl]-4,4-dimethylpent-1-en-3-one 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 1-(3,4-dihydro-3-m-tolyl-2-(1H-1,2,4-triazol-1-yl)quinazolin-4-yl)-3,3-dimethylbutan-2-one
  参考文献：
  名称：

  Synthesis, Fungicidal Activity, and Sterol 14α-Demethylase Binding Interaction of 2-Azolyl-3,4-dihydroquinazolines on Penicillium digitatum

  摘要：

  A series of new 2-azolyl-3,4-dihydroquinazolines 6 was synthesized by direct cyclization of imidazole or 1,2,4-triazole with carbodiimides 4, which were obtained from aza-Wittig reaction of iminophosphorane 3 with isocyanate. The preliminary bioassay results demonstrated that most of the 2-imidazolyl-3,4-dihydroquinazolines 6a-6i exhibited good to significant fungicidal activity against Penicillium digitatum, whereas 2-triazolyl-3,4-dihydroquinazolines 6j-6t exhibited low fungicidal activity. Some of the 2-imidazolyl-3,4-dihydroquinazolines 6a-6i also exhibited strong binding interaction with the cytochrome P450-dependent sterol 14 alpha-demethylase (CYP51). For example, compound 6e showed the best fungicidal activity against P. digitatum with IC50 = 4.14 mu g/mL and the best CYP51 binding activity with K-d = 0.34 mu g/mL, both superior to those of the agricultural fungicide triadimefon.

  DOI：

  10.1021/jf305355u

文献信息

• Synthesis, Fungicidal Activity, and Sterol 14α-Demethylase Binding Interaction of 2-Azolyl-3,4-dihydroquinazolines on Penicillium digitatum
  作者：Wen-Jin Li、Qian Li、De-Li Liu、Ming-Wu Ding

  DOI：10.1021/jf305355u

  日期：2013.2.20

  A series of new 2-azolyl-3,4-dihydroquinazolines 6 was synthesized by direct cyclization of imidazole or 1,2,4-triazole with carbodiimides 4, which were obtained from aza-Wittig reaction of iminophosphorane 3 with isocyanate. The preliminary bioassay results demonstrated that most of the 2-imidazolyl-3,4-dihydroquinazolines 6a-6i exhibited good to significant fungicidal activity against Penicillium digitatum, whereas 2-triazolyl-3,4-dihydroquinazolines 6j-6t exhibited low fungicidal activity. Some of the 2-imidazolyl-3,4-dihydroquinazolines 6a-6i also exhibited strong binding interaction with the cytochrome P450-dependent sterol 14 alpha-demethylase (CYP51). For example, compound 6e showed the best fungicidal activity against P. digitatum with IC50 = 4.14 mu g/mL and the best CYP51 binding activity with K-d = 0.34 mu g/mL, both superior to those of the agricultural fungicide triadimefon.