1-(2',4',5'-trimethoxybenzyl)-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroisoquinoline | 72943-40-9

• 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: 1-(2',4',5'-trimethoxybenzyl)-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 6,7-bis(phenylmethoxy)-1-[(2,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline
• CAS: 72943-40-9
• 化学式: C₃₃H₃₅NO₅
• 分子量: 525.645
• InChiKey: GZUCOVQFJFCTMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：
  0.27
• 拓扑面积：
  58.18
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(2',4',5'-trimethoxybenzyl)-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroisoquinoline 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以71%的产率得到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 sodium tetrahydroborate 、 碳酸氢钠 、 三氯氧磷 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 35.0h， 生成 1-(2',4',5'-trimethoxybenzyl)-6,7-bis(benzyloxy)-1,2,3,4-tetrahydroisoquinoline
  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

文献信息

• MILLER D. D.; BOSSART J. F.; MAYO J. R.; FELLER D. R., J. MED. CHEM., 1980, 23, NO 3, 331-333
  作者：MILLER D. D.、 BOSSART J. F.、 MAYO J. R.、 FELLER D. R.

  DOI：——

  日期：——