Dibenzyl-(4-phenyl-2H-chromen-2-ylmethyl)-amine | 77385-91-2

• 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: Dibenzyl-(4-phenyl-2H-chromen-2-ylmethyl)-amine
• 英文别名: 2-(N,N-Dibenzylaminomethyl)-4-phenyl-3-chromene；N,N-dibenzyl-1-(4-phenyl-2H-chromen-2-yl)methanamine
• CAS: 77385-91-2
• 化学式: C₃₀H₂₇NO
• 分子量: 417.55
• InChiKey: JZTSXYXTIJXTRD-UHFFFAOYSA-N

物化性质

• 沸点：
  551.2±49.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Dibenzyl-(4-phenyl-2H-chromen-2-ylmethyl)-amine 在 10percent Pd/C 甲酸 、 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.0h， 生成 cis-2-(2,6-dimethoxy-phenoxy)-N-(4-phenyl-chroman-2-ylmethyl)acetamide
  参考文献：
  名称：

  Structure−Activity Relationships in 1,4-Benzodioxan-Related Compounds. 7. Selectivity of 4-Phenylchroman Analogues for α₁−Adrenoreceptor Subtypes

  摘要：

  WB4101 (1)-related compounds 5-10 were synthesized, and their biological profile at alpha(1)-adrenoreceptor (AR) subtypes and 5-HT1A serotoninergic receptors was assessed by binding assays in Chinese hamster ovary and HeLa cell membranes expressing the human cloned receptors. Moreover, their receptor selectivity was further determined in functional experiments in isolated rat prostate (alpha(1A)), vas deferens (alpha(1A)), aorta (alpha(1D)), and spleen (alpha(1B)). In functional assays, compound 5 was the most potent at alpha(1D)-ARs with a reversed selectivity profile (alpha(1D) > alpha(1A) > alpha(1B)) relative to both prototype 1 and phendioxan (2) (alpha(1A) > alpha(1D) > alpha(1D)), whereas compound 8, bearing a carbonyl moiety at position 1, was the most potent at alpha(1)-ARs with a selectivity profile similar to that of prototypes. The least potent of the series was the trans isomer 6, suggesting that optimum alpha(1)-AR blocking activity in this series is associated with a cis relationship between the 2-side chain and the 4-phenyl ring rather than a trans relationship as previously observed for the 2-side chain and the 3-phenyl ring in 2 and related compounds. Binding affinity results were not in complete agreement with the selectivity profiles deriving from functional experiments. Although a firm explanation was not available, neutral and negative antagonism and receptor dimerization were considered as two possibilities to account for the difference between binding and functional affinities. Finally, compound 5 was selected for a modeling study in comparison with 1, mephendioxan (3), and open phendioxan (4) to achieve information on the physicochemical interactions that account for its high affinity toward alpha(1d/D)-ARs.

  DOI：

  10.1021/jm011066n
• 作为产物：
  描述：

  N,N-二苄基甘氨酸乙酯 、 、 、 、 苯基锂 生成 Dibenzyl-(4-phenyl-2H-chromen-2-ylmethyl)-amine
  参考文献：
  名称：

  Aminomethyl chromans

  摘要：

  一种具有厌食作用的通式（III）化合物，或其盐，其中R1、R2、R3和R4可以相同或不同，且均为氢或卤素原子，或三氟甲基，C1至C4烷基，C1至C4烷氧基，羟基，羧基，C1至C4烷氧羰基，氨基或乙酰胺基；R6为氢原子或C1至C4烷基；X为直链或支链烷基，碳原子数最多为4；R7和R8可以相同或不同，均为氢原子或C1至C4烷基，或R7与R8结合，使NR7R8形成5-7成员杂环。

  公开号：

  US04303656A1