3-phenyl-4aH,9H,9aH-indeno[1,2-e][1,2,4]triazin-9-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-phenyl-4aH,9H,9aH-indeno[1,2-e][1,2,4]triazin-9-one
• 英文别名: 3-phenylindeno[1,2-e][1,2,4]triazin-9-one
• 化学式: C₁₆H₉N₃O
• 分子量: 259.267
• InChiKey: OERHOWFXDDHRBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(3-aminophenyl)-4aH,9H,9aH-indeno[1,2-e][1,2,4]triazin-9-one 在 亚硝酸特丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以63%的产率得到3-phenyl-4aH,9H,9aH-indeno[1,2-e][1,2,4]triazin-9-one
  参考文献：
  名称：

  Synthesis and Monoamine Oxidase Inhibitory Activity of New Pyridazine-, Pyrimidine- and 1,2,4-Triazine-Containing Tricyclic Derivatives

  摘要：

  A number of condensed azines, mostly belonging to the families of indeno-fused pyridazines (1), pyrimidines (13), and 12,4-triazines (4, 5), were synthesized and evaluated in vitro as monoamine oxidase (MAO) A and B inhibitors. Most of them showed higher inhibition potency toward MAO-B, the most effective one being 3-(3-nitrophenyl)-9H-indeno[1,2-e] [1,2,4]triazin-9-one (4c), which displayed an IC50 value of 80 nM and proved to be I 0-fold more potent than its [2,1-e] fusion isomer 5. Replacing the 3-phenyl group of the known indeno[12-c]pyridazin-5-one MAO-B inhibitors with a flexible phenoxymethyl group enhanced the inhibitory potency. The inhibition data highlighted the importance of the aza-heterocyclic scaffold in affecting the MAO isoform selectivity. The 3-phenyl derivatives with type 1, 4, and 5 scaffolds were inhibitors of MAO-B with little or no MAO-A effect, whereas 2- or 3-phenyl derivatives of type 2 and 3 pyrimidine-containing fusion isomers inhibited both isoenzymes with a structure-dependent preference toward MAOA.

  DOI：

  10.1021/jm070728r