N-((2,2-diphenyl-1,3-dioxan-4-yl)methyl)-2-phenoxyethan-1-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-((2,2-diphenyl-1,3-dioxan-4-yl)methyl)-2-phenoxyethan-1-amine
• 英文别名: N-[(2,2-diphenyl-1,3-dioxan-4-yl)methyl]-2-phenoxyethanamine
• 化学式: C₂₅H₂₇NO₃
• 分子量: 389.494
• InChiKey: ABAMCUWCUXLAEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-((2,2-diphenyl-1,3-dioxan-4-yl)methyl)-2-phenoxyethan-1-amine 、 草酸 以 乙醚 为溶剂， 反应 24.0h， 以26%的产率得到N-((2,2-diphenyl-1,3-dioxan-4-yl)methyl)-2-phenoxyethan-1-ammonium hydrogen oxalate
  参考文献：
  名称：

  1,3-Dioxane as a scaffold for potent and selective 5-HT1AR agonist with in-vivo anxiolytic, anti-depressant and anti-nociceptive activity

  摘要：

  A series of compounds generated by ring expansion/opening and molecular elongation/simplification of the 1,3-dioxolane scaffold were prepared and tested for binding affinity at 5-HT1AR and alpha(1) adrenoceptors. The compounds with greater affinity were selected for further functional studies. N4(2,2-dipheny1-1,3-dioxan-5-yl)methyl)-2-(2-methoxyphenoxy)ethan-1-ammonium hydrogen oxalate (12) emerged as highly potent full agonist at the 5-HT1AR (pKi 5-HT1A = 8.8; pD(2) = 9.22, %E-max = 92). The pharmacokinetic data in rats showed that the orally administered 12 has a high biodistribution in the brain compartment. Thus, 12 was further investigated in-vivo, showing an anxiolytic and antidepressant effect. Moreover, in the formalin test, 12 was able to decrease the late response to the noxious stimulus, indicating a potent1Al use in the treatment of chronic pain. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.024
• 作为产物：
  描述：

  (2,2-diphenyl-1,3-dioxan-4-yl)methanol 在 吡啶 、 氯化亚砜 、 potassium iodide 作用下， 以 乙二醇甲醚 、 甲苯 为溶剂， 反应 24.75h， 生成 N-((2,2-diphenyl-1,3-dioxan-4-yl)methyl)-2-phenoxyethan-1-amine
  参考文献：
  名称：

  1,3-Dioxane as a scaffold for potent and selective 5-HT1AR agonist with in-vivo anxiolytic, anti-depressant and anti-nociceptive activity

  摘要：

  A series of compounds generated by ring expansion/opening and molecular elongation/simplification of the 1,3-dioxolane scaffold were prepared and tested for binding affinity at 5-HT1AR and alpha(1) adrenoceptors. The compounds with greater affinity were selected for further functional studies. N4(2,2-dipheny1-1,3-dioxan-5-yl)methyl)-2-(2-methoxyphenoxy)ethan-1-ammonium hydrogen oxalate (12) emerged as highly potent full agonist at the 5-HT1AR (pKi 5-HT1A = 8.8; pD(2) = 9.22, %E-max = 92). The pharmacokinetic data in rats showed that the orally administered 12 has a high biodistribution in the brain compartment. Thus, 12 was further investigated in-vivo, showing an anxiolytic and antidepressant effect. Moreover, in the formalin test, 12 was able to decrease the late response to the noxious stimulus, indicating a potent1Al use in the treatment of chronic pain. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.024