N-<<3,4-(dibenzyloxy)phenyl>ethyl>-2',4',5'-trimethoxyphenylacetamide | 72943-38-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: N-<<3,4-(dibenzyloxy)phenyl>ethyl>-2',4',5'-trimethoxyphenylacetamide
• 英文别名: N-{[3,4-(dibenzyloxy)phenyl]ethyl}-2',4',5'-trimethoxyphenylacetamide；N-[2-[3,4-bis(phenylmethoxy)phenyl]ethyl]-2-(2,4,5-trimethoxyphenyl)acetamide
• CAS: 72943-38-5
• 化学式: C₃₃H₃₅NO₆
• 分子量: 541.644
• InChiKey: WAZDOJSQSILBQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.25
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-<<3,4-(dibenzyloxy)phenyl>ethyl>-2',4',5'-trimethoxyphenylacetamide 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 32.0h， 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：

  (2,4,5-Trimethoxy-phenyl)-essigsaeure 在 氯化亚砜 、 碳酸氢钠 作用下， 以 氯仿 、 苯 为溶剂， 反应 18.0h， 生成 N-<<3,4-(dibenzyloxy)phenyl>ethyl>-2',4',5'-trimethoxyphenylacetamide
  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：——