2-(3-bromopropyl)-1,2,3,4-tetrahydroisoquinoline | 1146734-16-8

• 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-(3-bromopropyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(3-bromopropyl)-3,4-dihydro-1H-isoquinoline
• CAS: 1146734-16-8
• 化学式: C₁₂H₁₆BrN
• 分子量: 254.17
• InChiKey: HAJJCDSZWMADIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-吲哚酮 、 2-(3-bromopropyl)-1,2,3,4-tetrahydroisoquinoline 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 9.0h， 以44%的产率得到1-[3-(3,4-dihydroisoquinolin-2(1H)-yl)propyl]-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Synthesis of New Serotonin 5-HT₇ Receptor Ligands. Determinants of 5-HT₇/5-HT_1A Receptor Selectivity

  摘要：

  We report the synthesis of a new set of compounds of general structure I (1-20) with structural modifications in the pharmacophoric elements of the previously reported lead UCM-5600. The new derivatives have been evaluated for binding affinity at 5-HT7 and 5-HT1A receptors. The influence of the different structural features in terms of 5-HT7/5-HT1A receptor affinity and selectivity was analyzed by computational simulations of the complexes between compounds I and beta(2)-based 3-D models of these receptors. Compound 18 (HYD1 = 1,3-dihydro-2H-indol-2-one; spacer = -(CH2)(4)-; HYD2 + HYD3 = 3,4-dihydroisoquinolin-2(1H)-yl) exhibits high 5-HT7R affinity (K-i = 7 nM) and selectivity over the 5-HT1AR (31-fold), and has been characterized as a partial agonist of the human 5-HT7R.

  DOI：

  10.1021/jm8014553
• 作为产物：
  描述：

  四氢异喹啉 、 1,3-二溴丙烷 以 sodium hydroxide 、 丙酮 为溶剂， 反应 7.0h， 以25%的产率得到2-(3-bromopropyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis of New Serotonin 5-HT₇ Receptor Ligands. Determinants of 5-HT₇/5-HT_1A Receptor Selectivity

  摘要：

  We report the synthesis of a new set of compounds of general structure I (1-20) with structural modifications in the pharmacophoric elements of the previously reported lead UCM-5600. The new derivatives have been evaluated for binding affinity at 5-HT7 and 5-HT1A receptors. The influence of the different structural features in terms of 5-HT7/5-HT1A receptor affinity and selectivity was analyzed by computational simulations of the complexes between compounds I and beta(2)-based 3-D models of these receptors. Compound 18 (HYD1 = 1,3-dihydro-2H-indol-2-one; spacer = -(CH2)(4)-; HYD2 + HYD3 = 3,4-dihydroisoquinolin-2(1H)-yl) exhibits high 5-HT7R affinity (K-i = 7 nM) and selectivity over the 5-HT1AR (31-fold), and has been characterized as a partial agonist of the human 5-HT7R.

  DOI：

  10.1021/jm8014553