5,6,8,9,10,14c-hexahydroindolo[3',2':3,4]pyrido[2,1-a]isoquinoline | 1217181-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 5,6,8,9,10,14c-hexahydroindolo[3',2':3,4]pyrido[2,1-a]isoquinoline
• 英文别名: 9,13-Diazapentacyclo[11.8.0.02,10.03,8.016,21]henicosa-2(10),3,5,7,16,18,20-heptaene
• CAS: 1217181-11-7
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: RKVOQFDZLRUOCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6,8,9,10,14c-hexahydroindolo[3',2':3,4]pyrido[2,1-a]isoquinoline 、 碘甲烷 以 乙腈 为溶剂， 反应 24.0h， 以69%的产率得到7-methyl-5,6,8,9,10,14c-hexahydroindolo[3',2':3,4]pyrido[2,1-a]isoquinolin-7-ium iodide
  参考文献：
  名称：

  Dopamine Receptor Ligands. Part 18: Modification of the Structural Skeleton of Indolobenzazecine-Type Dopamine Receptor Antagonists

  摘要：

  On the basis of the D(1/5)-selective dopamine antagonist LE 300 (1), an indolo[3,2-f]benzazecine derivative, we changed the annulation pattern of the heterocycles. The target compounds represent novel heterocyclic ring systems. The most constrained indolo[4,3a,3-ef]benzazecine 2 was inactive, but the indolo[4,3a,3-fg]benzazacycloundecene 3 showed antagonistic properties (functional Ca(2+) assay) with nanomolar affinities (radioligand binding) for all dopamine receptor subtypes, whereas the indolo[2,3-f]benzazecine 4 displayed a selectivity profile similar to 3 but with decreased affinities.

  DOI：

  10.1021/jm901291r
• 作为产物：
  描述：

  2-(2-氨基乙基)吲哚 、 2-(2-溴乙基)苯甲醛 在 三氟乙酸 、 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 5,6,8,9,10,14c-hexahydroindolo[3',2':3,4]pyrido[2,1-a]isoquinoline
  参考文献：
  名称：

  Dopamine Receptor Ligands. Part 18: Modification of the Structural Skeleton of Indolobenzazecine-Type Dopamine Receptor Antagonists

  摘要：

  On the basis of the D(1/5)-selective dopamine antagonist LE 300 (1), an indolo[3,2-f]benzazecine derivative, we changed the annulation pattern of the heterocycles. The target compounds represent novel heterocyclic ring systems. The most constrained indolo[4,3a,3-ef]benzazecine 2 was inactive, but the indolo[4,3a,3-fg]benzazacycloundecene 3 showed antagonistic properties (functional Ca(2+) assay) with nanomolar affinities (radioligand binding) for all dopamine receptor subtypes, whereas the indolo[2,3-f]benzazecine 4 displayed a selectivity profile similar to 3 but with decreased affinities.

  DOI：

  10.1021/jm901291r

文献信息

• Dopamine Receptor Ligands. Part 18: Modification of the Structural Skeleton of Indolobenzazecine-Type Dopamine Receptor Antagonists
  作者：Dina Robaa、Christoph Enzensperger、Shams El Din Abul Azm、El Sayeda El Khawass、Ola El Sayed、Jochen Lehmann

  DOI：10.1021/jm901291r

  日期：2010.3.25

  On the basis of the D(1/5)-selective dopamine antagonist LE 300 (1), an indolo[3,2-f]benzazecine derivative, we changed the annulation pattern of the heterocycles. The target compounds represent novel heterocyclic ring systems. The most constrained indolo[4,3a,3-ef]benzazecine 2 was inactive, but the indolo[4,3a,3-fg]benzazacycloundecene 3 showed antagonistic properties (functional Ca(2+) assay) with nanomolar affinities (radioligand binding) for all dopamine receptor subtypes, whereas the indolo[2,3-f]benzazecine 4 displayed a selectivity profile similar to 3 but with decreased affinities.