1-diethoxymethyl-2-hydroxymethylindole-5-carbonitrile | 313972-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-diethoxymethyl-2-hydroxymethylindole-5-carbonitrile
• 英文别名: 1-(Diethoxymethyl)-2-(hydroxymethyl)indole-5-carbonitrile
• CAS: 313972-74-6
• 化学式: C₁₅H₁₈N₂O₃
• 分子量: 274.32
• InChiKey: DHXSWZCCNAWCPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-diethoxymethyl-2-hydroxymethylindole-5-carbonitrile 在 四氯化碳 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以45%的产率得到2-chloromethyl-1-diethoxymethylindole-5-carbonitrile
  参考文献：
  名称：

  Cyanoindole Derivatives as Highly Selective Dopamine D₄ Receptor Partial Agonists:  Solid-Phase Synthesis, Binding Assays, and Functional Experiments

  摘要：

  Traceless linking of diethoxymethyl (DEM)-protected 5- and 6-cyanoindoles and subsequent incorporation of phenylpiperazine derivatives led to the 2- and 3-piperazinylmethyl-substituted cyanoindoles 3a-m. Dopamine receptor binding studies on the final products 3a-m clearly indicated strong and selective recognition of the D-4 subtype which is known as a promising target for the treatment of neuropsychiatric disorders. The most interesting binding properties were observed for the 2-aminomethyl-5-cyanoindoles FAUC 299 (3f) and FAUC 316 (3j) (K-i = 0.52 and 1.0 nM, respectively) when the fluoro derivative 3j proved extraordinary selectivity over D-1, D-2long, D-2short, and D-9 (>8600). To determine ligand efficacy, mitogenesis experiments were performed indicating partial agonist effects for the test compounds 3fj (35% and 30%, when compared to the full agonist quinpirole).

  DOI：

  10.1021/jm0009989
• 作为产物：
  描述：

  2-(hydroxymethyl)indole-5-carbonitrile 在 咪唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 1-diethoxymethyl-2-hydroxymethylindole-5-carbonitrile
  参考文献：
  名称：

  Cyanoindole Derivatives as Highly Selective Dopamine D₄ Receptor Partial Agonists:  Solid-Phase Synthesis, Binding Assays, and Functional Experiments

  摘要：

  Traceless linking of diethoxymethyl (DEM)-protected 5- and 6-cyanoindoles and subsequent incorporation of phenylpiperazine derivatives led to the 2- and 3-piperazinylmethyl-substituted cyanoindoles 3a-m. Dopamine receptor binding studies on the final products 3a-m clearly indicated strong and selective recognition of the D-4 subtype which is known as a promising target for the treatment of neuropsychiatric disorders. The most interesting binding properties were observed for the 2-aminomethyl-5-cyanoindoles FAUC 299 (3f) and FAUC 316 (3j) (K-i = 0.52 and 1.0 nM, respectively) when the fluoro derivative 3j proved extraordinary selectivity over D-1, D-2long, D-2short, and D-9 (>8600). To determine ligand efficacy, mitogenesis experiments were performed indicating partial agonist effects for the test compounds 3fj (35% and 30%, when compared to the full agonist quinpirole).

  DOI：

  10.1021/jm0009989