3-<<<2-(2,6-dimethoxyphenoxy)ethyl>amino>methyl>-4-chromanone | 116635-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-<<<2-(2,6-dimethoxyphenoxy)ethyl>amino>methyl>-4-chromanone
• 英文别名: 3-({[2-(2,6-dimethoxyphenoxy)ethyl]amino}methyl)-4-chromanone；3-[[2-(2,6-dimethoxyphenoxy)ethylamino]methyl]-2,3-dihydrochromen-4-one
• CAS: 116635-68-8
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: YMAVEYCFYXTMQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.02
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-<<<2-(2,6-dimethoxyphenoxy)ethyl>amino>methyl>-4-chromanone 在 溶剂黄146 、 锌 作用下， 反应 6.0h， 以12%的产率得到3-<<<2-(2,6-dimethoxyphenoxy)ethyl>amino>methyl>chromane
  参考文献：
  名称：

  Structure-activity relationships in 1,4-benzodioxan-related compounds. Investigation on the role of the dehydrodioxane ring on .alpha.1-adrenoreceptor blocking activity

  摘要：

  Several analogues of 2-[[[2-(2,6-dimethoxyphenoxy)ethyl]amino]methyl]-1,4-benzodioxa n (WB 4101, 1) were prepared and evaluated for their blocking activity on alpha 1- and alpha 2-adrenoreceptors in the isolated rat vas deferens. The results were compared with those obtained for 1 and benoxathian (2). It was shown that the two oxygens at positions 1 and 4 may have a different role in receptor binding. It seems that the oxygen at position 4 as such does not contribute to the binding while it is important in stabilizing an optimal conformation for drug-receptor interaction mechanism. On the other hand, the oxygen at position 1 might interact with a receptor polar pocket of reduced size by way of a donor-acceptor dipolar interaction. Furthermore, it was shown that replacement of the dehydrodioxane ring of 1 by a phenyl or a pyrrole nucleus causes a significant decrease in activity.

  DOI：

  10.1021/jm00120a009
• 作为产物：
  描述：

  聚合甲醛 、 2,3-二氢苯并吡喃-4-酮 、 2-(2,6-dimethoxy-phenoxy)ethylamine hydrochloride 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以75%的产率得到3-<<<2-(2,6-dimethoxyphenoxy)ethyl>amino>methyl>-4-chromanone
  参考文献：
  名称：

  Structure-activity relationships in 1,4-benzodioxan-related compounds. Investigation on the role of the dehydrodioxane ring on .alpha.1-adrenoreceptor blocking activity

  摘要：

  Several analogues of 2-[[[2-(2,6-dimethoxyphenoxy)ethyl]amino]methyl]-1,4-benzodioxa n (WB 4101, 1) were prepared and evaluated for their blocking activity on alpha 1- and alpha 2-adrenoreceptors in the isolated rat vas deferens. The results were compared with those obtained for 1 and benoxathian (2). It was shown that the two oxygens at positions 1 and 4 may have a different role in receptor binding. It seems that the oxygen at position 4 as such does not contribute to the binding while it is important in stabilizing an optimal conformation for drug-receptor interaction mechanism. On the other hand, the oxygen at position 1 might interact with a receptor polar pocket of reduced size by way of a donor-acceptor dipolar interaction. Furthermore, it was shown that replacement of the dehydrodioxane ring of 1 by a phenyl or a pyrrole nucleus causes a significant decrease in activity.

  DOI：

  10.1021/jm00120a009