3,4,5,7,8,12b-hexahydroimidazo[4',5':3,4]pyrido[2,1-a]isoquinoline | 1440509-71-6

• 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: 3,4,5,7,8,12b-hexahydroimidazo[4',5':3,4]pyrido[2,1-a]isoquinoline
• 英文别名: 10,14,16-Triazatetracyclo[8.7.0.02,7.013,17]heptadeca-2,4,6,13(17),15-pentaene；10,14,16-triazatetracyclo[8.7.0.02,7.013,17]heptadeca-2,4,6,13(17),15-pentaene
• CAS: 1440509-71-6
• 化学式: C₁₄H₁₅N₃
• 分子量: 225.293
• InChiKey: CWTQVGJTNOSXCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4,5,7,8,12b-hexahydroimidazo[4',5':3,4]pyrido[2,1-a]isoquinoline 在 potassium carbonate 作用下， 以 水 、 异丙醇 、 丙酮 为溶剂， 反应 89.0h， 生成 3-(tert-butoxycarbonyl)-6-methyl-3,4,5,7,8,12b-hexahydroimidazo[4',5':3,4]pyrido[2,1-a]isoquinolin-6-ium iodide
  参考文献：
  名称：

  新型杂环系统的合成和生物活性：咪唑并[4',5':3,4]吡啶并[2,1-a]异喹啉和咪唑并[4,5-f][3]苯扎西辛

  摘要：

  Derivatives of two novel heterocyclic ring systems were synthesized and their affinities for dopamine receptors were measured. The compounds were obtained by reacting histamine with 2-(2-bromoethyl)benzaldehyde including an atypical Pictet-Spengler condensation, which afforded basic and not the usual neutral or acidic conditions. The resulting imidazo[4',5':3,4]pyrido[2,1-a]isoquinoline derivative 4 was Boc protected at the most basic imidazole nitrogen, the isoquinoline nitrogen then quaternized by using methyl iodide and the tetracyclic isoquinolinium salt was both deprotected and cleaved under Birch conditions in one step to give a tricyclic imidazo[4,5-f][3]benzazecine derivative (3) by opening two 6-membered heterocycles towards one 10-membered. Radioligand binding studies showed a significant affinity of the moderately constrained 3 but not of 4 for dopamine receptors. Similar to the analogous indolo-benzazecine LE300, a preference of 3 for the D-1 receptor family was observed, but with some loss of affinity over all.

  DOI：

  10.3987/com-12-12574
• 作为产物：
  描述：

  2-(2-溴乙基)苯甲醛 在 氨 作用下， 以 二氯甲烷 为溶剂， 反应 24.08h， 生成 3,4,5,7,8,12b-hexahydroimidazo[4',5':3,4]pyrido[2,1-a]isoquinoline
  参考文献：
  名称：

  新型杂环系统的合成和生物活性：咪唑并[4',5':3,4]吡啶并[2,1-a]异喹啉和咪唑并[4,5-f][3]苯扎西辛

  摘要：

  Derivatives of two novel heterocyclic ring systems were synthesized and their affinities for dopamine receptors were measured. The compounds were obtained by reacting histamine with 2-(2-bromoethyl)benzaldehyde including an atypical Pictet-Spengler condensation, which afforded basic and not the usual neutral or acidic conditions. The resulting imidazo[4',5':3,4]pyrido[2,1-a]isoquinoline derivative 4 was Boc protected at the most basic imidazole nitrogen, the isoquinoline nitrogen then quaternized by using methyl iodide and the tetracyclic isoquinolinium salt was both deprotected and cleaved under Birch conditions in one step to give a tricyclic imidazo[4,5-f][3]benzazecine derivative (3) by opening two 6-membered heterocycles towards one 10-membered. Radioligand binding studies showed a significant affinity of the moderately constrained 3 but not of 4 for dopamine receptors. Similar to the analogous indolo-benzazecine LE300, a preference of 3 for the D-1 receptor family was observed, but with some loss of affinity over all.

  DOI：

  10.3987/com-12-12574

文献信息

• Synthesis and Biological Activity of Novel Heterocyclic Ring Systems: Imidazo[4’,5’:3,4]pyrido[2,1-a]isoquinolines and Imidazo[4,5-f][3]benzazecines
  作者：Jochen Lehmann、Robert Otto、Christoph Enzensperger

  DOI：10.3987/com-12-12574

  日期：——

  Derivatives of two novel heterocyclic ring systems were synthesized and their affinities for dopamine receptors were measured. The compounds were obtained by reacting histamine with 2-(2-bromoethyl)benzaldehyde including an atypical Pictet-Spengler condensation, which afforded basic and not the usual neutral or acidic conditions. The resulting imidazo[4',5':3,4]pyrido[2,1-a]isoquinoline derivative 4 was Boc protected at the most basic imidazole nitrogen, the isoquinoline nitrogen then quaternized by using methyl iodide and the tetracyclic isoquinolinium salt was both deprotected and cleaved under Birch conditions in one step to give a tricyclic imidazo[4,5-f][3]benzazecine derivative (3) by opening two 6-membered heterocycles towards one 10-membered. Radioligand binding studies showed a significant affinity of the moderately constrained 3 but not of 4 for dopamine receptors. Similar to the analogous indolo-benzazecine LE300, a preference of 3 for the D-1 receptor family was observed, but with some loss of affinity over all.