1-(6-chloro-3,4-dihydro-3-isopropyl-2-(1H-1,2,4-triazol-1-yl)-quinazolin-4-yl)propan-2-one | 1422541-88-5

• 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-(6-chloro-3,4-dihydro-3-isopropyl-2-(1H-1,2,4-triazol-1-yl)-quinazolin-4-yl)propan-2-one
• 英文别名: 1-[6-chloro-3-propan-2-yl-2-(1,2,4-triazol-1-yl)-4H-quinazolin-4-yl]propan-2-one
• CAS: 1422541-88-5
• 化学式: C₁₆H₁₈ClN₅O
• 分子量: 331.805
• InChiKey: RPGHLTVXWVYGMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 1-(6-chloro-3,4-dihydro-3-isopropyl-2-(1H-1,2,4-triazol-1-yl)-quinazolin-4-yl)propan-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