WB 4346 | 40516-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: WB 4346
• 英文别名: 2-<<<2-(2,6-dimethoxyphenoxy)ethyl>amino>methyl>chromane；2-({[2-(2,6-dimethoxyphenoxy)ethyl]amino}methyl)chromane；N-(3,4-dihydro-2H-chromen-2-ylmethyl)-2-(2,6-dimethoxyphenoxy)ethanamine
• CAS: 40516-01-6
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: CYCKGHZMZZHNDN-UHFFFAOYSA-N

物化性质

• 沸点：
  482.0±40.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯并二氢吡喃-2-羧酸 在 盐酸 、 dimethyl sulfide borane 、 氯甲酸乙酯 、 三乙胺 作用下， 反应 29.33h， 生成 WB 4346
  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

文献信息

• Structure-activity relationships in 1,4-benzodioxan-related compounds. Investigation on the role of the dehydrodioxane ring on .alpha.1-adrenoreceptor blocking activity
  作者：Maria Pigini、Livio Brasili、Mario Giannella、Dario Giardina、Ugo Gulini、Wilma Quaglia、Carlo Melchiorre

  DOI：10.1021/jm00120a009

  日期：1988.12

  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.