(2S,3R)-3-[[2-(2,6-dimethoxyphenoxy)ethylamino]methyl]-2-phenyl-2,3-dihydrochromen-4-one | 130905-05-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2S,3R)-3-[[2-(2,6-dimethoxyphenoxy)ethylamino]methyl]-2-phenyl-2,3-dihydrochromen-4-one
• CAS: 130905-05-4
• 化学式: C₂₆H₂₇NO₅
• 分子量: 433.504
• InChiKey: PUAAUDBUJSSOLX-NBGIEHNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 2-(2,6-dimethoxy-phenoxy)ethylamine hydrochloride 、 黄烷酮 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (2S,3R)-3-[[2-(2,6-dimethoxyphenoxy)ethylamino]methyl]-2-phenyl-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  Structure−Activity Relationships in 1,4-Benzodioxan-Related Compounds. 6. Role of the Dioxane Unit on Selectivity for α₁-Adrenoreceptor Subtypes

  摘要：

  WB 4101-related benzodioxans 3-9 were synthesized, and their biological profiles at alpha(1)-adrenoreceptor subtypes and 5-HT1A serotoninergic receptors were assessed by binding assays in CHO and HeLa cells membranes expressing the human cloned receptors. Furthermore, receptor selectivity of selected benzodioxan derivatives was further determined in functional experiments in isolated rat vas deferens ((alpha(1A)) and aorta (alpha(1D)) and guinea pig spleen (alpha(1B)), in additional receptor binding assays in rat cortex membranes containing alpha(2)-adrenoreceptors and 5-HT2 serotoninergic receptors, and in rat striatum membranes containing D-2 dopaminergic receptors. An analysis of the results of receptor binding experiments for benzodioxan-modified derivatives 3-9 showed high affinity and selectivity toward the alpha(1a)-adrenoreceptor subtype for compounds 3-5 and 7 and a reversed selectivity profile for 9, which was a selective aid antagonist. Furthermore, the majority of structural modifications performed on the prototype 1 (WB 4101) led to a marked decrease in the affinity for 5-HT1A serotoninergic receptors, which may have relevance in the design of selective alpha(1A)-adrenoreceptor antagonists. The exception to these findings was the chromene derivative 8, which exhibited a 5-HT1A partial agonist profile.

  DOI：

  10.1021/jm9910324

文献信息

• Structure-activity relationships in 1,4-benzodioxan related compounds. 3. 3-Phenyl analogs of 2-[[[2-(2,6-dimethoxyphenoxy)ethyl]amino]methyl]-1,4-benzodioxan (WB 4101) as highly selective .alpha.1-adrenoreceptor antagonists
  作者：Wilma Quaglia、Maria Pigini、Mario Giannella、Carlo Melchiorre

  DOI：10.1021/jm00173a004

  日期：1990.11