2-methyl-9H-indeno[2,1-d]pyrimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-methyl-9H-indeno[2,1-d]pyrimidine
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: BJDSRCZFZOYBSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-9H-indeno[2,1-d]pyrimidine 在 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 0.33h， 以50%的产率得到2-methyl-9H-indeno[2,1-d]pyrimidin-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
• 作为产物：
  描述：

  1-(N,N-dimethylaminomethyliden)indan-2-one 、 盐酸乙脒 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以47%的产率得到2-methyl-9H-indeno[2,1-d]pyrimidine
  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

文献信息

• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：Universal Display Corporation

  公开号：US20160233435A1

  公开（公告）日：2016-08-11

  A novel compounds useful as hosts for phosphorescent emitters in OLEDs is disclosed.

  本发明揭示了一种在OLEDs中作为磷光发射体宿主有用的新化合物。
• Synthesis and Monoamine Oxidase Inhibitory Activity of New Pyridazine-, Pyrimidine- and 1,2,4-Triazine-Containing Tricyclic Derivatives
  作者：Andrea Carotti、Marco Catto、Francesco Leonetti、Francesco Campagna、Ramón Soto-Otero、Estefanía Méndez-Álvarez、Ulrike Thull、Bernard Testa、Cosimo Altomare

  DOI：10.1021/jm070728r

  日期：2007.11.1

  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.