2,8,9,13b-tetrahydro-6H-isoquino[2,1-b]pyrrolo[4,3,2-de]isoquinoline | 1217181-06-0

• 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: 2,8,9,13b-tetrahydro-6H-isoquino[2,1-b]pyrrolo[4,3,2-de]isoquinoline
• 英文别名: 11,18-Diazapentacyclo[11.6.1.02,11.03,8.017,20]icosa-1(19),3,5,7,13(20),14,16-heptaene
• CAS: 1217181-06-0
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: VAGUGVHWYBXLRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2,8,9,13b-tetrahydro-6H-isoquino[2,1-b]pyrrolo[4,3,2-de]isoquinoline 、 氯甲酸乙酯 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以27%的产率得到ethyl 4,5,6,7-tetrahydroindolo[4,3a,3-ef][3]benzazecine-5-carboxylate
  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-(indol-4-ylmethyl)-3,4-dihydroisoquinolinium bromide 在 盐酸 、 氨 作用下， 以 水 为溶剂， 反应 4.0h， 以0.86 g的产率得到2,8,9,13b-tetrahydro-6H-isoquino[2,1-b]pyrrolo[4,3,2-de]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.