benoxathian | 92642-94-9

• 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: benoxathian
• 英文别名: N-(2,3-dihydro-1,4-benzoxathiin-2-ylmethyl)-2-(2,6-dimethoxyphenoxy)ethanamine
• CAS: 92642-94-9
• 化学式: C₁₉H₂₃NO₄S
• 分子量: 361.462
• InChiKey: QAUVAHYHKLRJCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benoxathian 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 20.0h， 以40%的产率得到2-<<<2-(2,6-dimethoxyphenoxy)ethyl>amino>methyl>-1,4-benzoxathian S,S-dioxide
  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：

  N-[2-(2,6-dimethoxyphenoxy)ethyl]-2,3-dihydro-1,4-benzoxathiine-2-carboxamide 在 dimethyl sulfide borane 作用下， 以 二乙二醇二甲醚 为溶剂， 生成 benoxathian
  参考文献：
  名称：

  2-[[[[[2-（2,6-二甲氧基苯氧基）乙基]氨基]-甲基] -1,4-苯并噻吨：一种对α1-肾上腺素受体具有高效力和选择性的新型拮抗剂。

  摘要：

  DOI：

  10.1021/jm00378a001

文献信息

• CASSINELLI A.; QUAGLIA W.; BRASILI L.; GIARDINA D.; GULINI U.; MELCHIORRE+, EUR. J. MED. CHEM., 22,(1987) N 1, 23-26
  作者：CASSINELLI A.、 QUAGLIA W.、 BRASILI L.、 GIARDINA D.、 GULINI U.、 MELCHIORRE+

  DOI：——

  日期：——
• PIGINI, MARIA;BRASILI, LIVIO;GIANNELLA, MARIO;GIARDINA, DARIO;GULINI, UGO+
  作者：PIGINI, MARIA、BRASILI, LIVIO、GIANNELLA, MARIO、GIARDINA, DARIO、GULINI, UGO+

  DOI：——

  日期：——
• 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.
• 2-[[[2-(2,6-Dimethoxyphenoxy)ethyl]amino]methyl]-1,4-benzoxathian: a new antagonist with high potency and selectivity towards .alpha.1-adrenoreceptors
  作者：Carlo Melchiorre、Livio Brasili、Dario Giardina、Maria Pigini、Giovannella Strappaghetti

  DOI：10.1021/jm00378a001

  日期：1984.12