6,7-bis(benzyloxy)-1-(2,4,5-trimethoxybenzyl)-3,4-dihydroisoquinoline | 72943-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6,7-bis(benzyloxy)-1-(2,4,5-trimethoxybenzyl)-3,4-dihydroisoquinoline
• CAS: 72943-39-6
• 化学式: C₃₃H₃₃NO₅
• 分子量: 523.629
• InChiKey: TWKGDENFMQWBAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  58.51
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6,7-bis(benzyloxy)-1-(2,4,5-trimethoxybenzyl)-3,4-dihydroisoquinoline 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 30.0h， 生成 1-(2',4',5'-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride
  参考文献：
  名称：

  Synthesis, .beta.-adrenergic activity, and platelet antiaggregatory activity of a positional isomer of trimetoquinol: 1-(2',4',5'-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

  摘要：

  A positional isomer of trimetoquinol (1), 1-(2',4',5'-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (3), was synthesized and found to possess less beta-adrenergic activity than 1 in isolated guinea pig atrial and tracheal preparations. The analogue 3 was an effective antiaggregatory agent in human and rabbit platelet-rich plasma preparations, while 1 was effective only as an inhibitor of arachidonic acid induced aggregation in human platelets. These findings indicate that both qualitative and quantitative differences in biological activity have occurred as a result of changing the position of the methoxy groups on the 1-benzyl substituent of 1.

  DOI：

  10.1021/jm00177a027
• 作为产物：
  描述：

  3,4-di(benzyloxy)phenethylamine 在 碳酸氢钠 、 三氯氧磷 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 17.0h， 生成 6,7-bis(benzyloxy)-1-(2,4,5-trimethoxybenzyl)-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Synthesis, .beta.-adrenergic activity, and platelet antiaggregatory activity of a positional isomer of trimetoquinol: 1-(2',4',5'-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

  摘要：

  A positional isomer of trimetoquinol (1), 1-(2',4',5'-trimethoxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (3), was synthesized and found to possess less beta-adrenergic activity than 1 in isolated guinea pig atrial and tracheal preparations. The analogue 3 was an effective antiaggregatory agent in human and rabbit platelet-rich plasma preparations, while 1 was effective only as an inhibitor of arachidonic acid induced aggregation in human platelets. These findings indicate that both qualitative and quantitative differences in biological activity have occurred as a result of changing the position of the methoxy groups on the 1-benzyl substituent of 1.

  DOI：

  10.1021/jm00177a027