2-(aminomethyl)-1,4-naphtho<2,3-b>dioxan | 113777-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(aminomethyl)-1,4-naphtho<2,3-b>dioxan
• 英文别名: 2-Aminomethyl-naphtho<2,3-b>-1,4-benzodioxan；C-(2,3-dihydro-naphtho[2,3-b][1,4]dioxin-2-yl)-methylamine
• CAS: 113777-39-2
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: XXSTTWJUEZQAJD-UHFFFAOYSA-N

物化性质

• 沸点：
  374.4±21.0 °C(predicted)
• 密度：
  1.214±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(aminomethyl)-1,4-naphtho<2,3-b>dioxan 、 N-<4-(tosyloxy)butyl>-3,3-tetramethyleneglutarimide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以42.2%的产率得到8-(4-{[(2,3-dihydronaphtho[2,3-b]dioxin-2-yl)methyl]amino}butyl)-8-azaspiro[4.5]decane-7,9-dione
  参考文献：
  名称：

  Graphics computer-aided receptor mapping as a predictive tool for drug design: development of potent, selective, and stereospecific ligands for the 5-HT1A receptor

  摘要：

  A conformational study of four 5-HT1A (serotonin) receptor ligands ((R-(-)-methiothepin, spiperone, (S)-(-)-propranolol, and buspirone) led to the definition of a pharmacophore and a three-dimensional map of the 5-HT1A antagonist recognition site. These models were used to design new compounds and successfully predict their potency, stereospecificity, and selectivity. For example, 8-[4-[(1,4-benzodioxan-2-ylmethyl)amino] butyl]-8-azaspiro[4.5]decane-7,9-dione (1, MDL 72832) has nanomolar affinity (pIC50 = 9.14) for the 5-HT1A binding site in rat frontal cortex. As predicted, the S-(-) enantiomer of 1 was more active than its R-(+) enantiomer (pIC50 = 9.21 and 7.66, respectively) and a naphthalene analogue of 1 displayed the expected improved selectivity.

  DOI：

  10.1021/jm00401a007