5-chloro-2-[5-(2-fluorophenyl)-1H-1,2,4-triazol-3-yl]phenol | 165679-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-2-[5-(2-fluorophenyl)-1H-1,2,4-triazol-3-yl]phenol
• CAS: 165679-59-4
• 化学式: C₁₄H₉ClFN₃O
• 分子量: 289.696
• InChiKey: VKOZBMNMIKANMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三光气 、 5-chloro-2-[5-(2-fluorophenyl)-1H-1,2,4-triazol-3-yl]phenol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到8-Chloro-2-(2-fluorophenyl)-[1,2,4]triazolo[1,5-c][1,3]benzoxazin-5-one
  参考文献：
  名称：

  Synthesis of Some 2-Aryl-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones as Tools To Define the Essential Pharmacophoric Descriptors of a Benzodiazepine Receptor Ligand

  摘要：

  The synthesis and benzodiazepine receptor (BZR) affinity of some 1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones, 2-22, are reported. Compounds 2-22 are devoid of the proton donor group, which according to a BZR schematic model was one of the pharmacophoric descriptors for receptor-ligand interaction. The binding data show that 2-(2-fluorophenyl)-9-chloro-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-one (12) and some other compounds display nanomolar BZR affinity, indicating that the hydrogen donor group is not essential for the anchoring of 6,6,5-tricyclic systems to the BZR but only affects the potency of a ligand.

  DOI：

  10.1021/jm00012a020
• 作为产物：
  描述：

  4-chloro-N-(2-fluorobenzoyl)-2-hydroxybenzamide 在 一水合肼 作用下， 生成 5-chloro-2-[5-(2-fluorophenyl)-1H-1,2,4-triazol-3-yl]phenol
  参考文献：
  名称：

  Synthesis of Some 2-Aryl-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones as Tools To Define the Essential Pharmacophoric Descriptors of a Benzodiazepine Receptor Ligand

  摘要：

  The synthesis and benzodiazepine receptor (BZR) affinity of some 1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones, 2-22, are reported. Compounds 2-22 are devoid of the proton donor group, which according to a BZR schematic model was one of the pharmacophoric descriptors for receptor-ligand interaction. The binding data show that 2-(2-fluorophenyl)-9-chloro-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-one (12) and some other compounds display nanomolar BZR affinity, indicating that the hydrogen donor group is not essential for the anchoring of 6,6,5-tricyclic systems to the BZR but only affects the potency of a ligand.

  DOI：

  10.1021/jm00012a020