2,4-bis(3-methoxyphenyl)-2,4-dimethyl-1,3,5-trioxazatriquinane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4-bis(3-methoxyphenyl)-2,4-dimethyl-1,3,5-trioxazatriquinane
• 英文别名: (1S,3R,4S,6S,7S)-3,6-bis(3-methoxyphenyl)-3,6-dimethyl-2,5,8-trioxa-10-azatricyclo[5.2.1.04,10]decane
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: BISYCXYJFMIOEX-KNOXWWKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-bis(3-methoxyphenyl)-2,4-dimethyl-1,3,5-trioxazatriquinane 在 丙烷-1-硫醇 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以61%的产率得到3,3'-(2,4-dimethyl-1,3,5-trioxazatriquinan-2,4-diyl)bisphenol
  参考文献：
  名称：

  Synthesis and Pharmacology of a Novel κ Opioid Receptor (KOR) Agonist with a 1,3,5-Trioxazatriquinane Skeleton

  摘要：

  We designed and synthesized the 1,3,5-trioxazatriquinane derivatives with m-hydroxyphenyl groups. These compounds include the phenethylamine structure within them, which is a common structure observed in morphinan derivatives like morphine. Among the synthesized compounds, (-)-8c with two m-hydroxyphenyl groups selectively bound and exerted full agonist activity toward the κ opioid receptor (KOR). Subcutaneously administered (-)-8c exhibited significant antinociceptive effects via the KOR in a dose-dependent manner. These results suggest the emergence of a novel class of KOR agonist.

  DOI：

  10.1021/ml5000542
• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 D(+)-10-樟脑磺酸 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 9.0h， 生成 2,4-bis(3-methoxyphenyl)-2,4-dimethyl-1,3,5-trioxazatriquinane
  参考文献：
  名称：

  Synthesis and Pharmacology of a Novel κ Opioid Receptor (KOR) Agonist with a 1,3,5-Trioxazatriquinane Skeleton

  摘要：

  We designed and synthesized the 1,3,5-trioxazatriquinane derivatives with m-hydroxyphenyl groups. These compounds include the phenethylamine structure within them, which is a common structure observed in morphinan derivatives like morphine. Among the synthesized compounds, (-)-8c with two m-hydroxyphenyl groups selectively bound and exerted full agonist activity toward the κ opioid receptor (KOR). Subcutaneously administered (-)-8c exhibited significant antinociceptive effects via the KOR in a dose-dependent manner. These results suggest the emergence of a novel class of KOR agonist.

  DOI：

  10.1021/ml5000542

文献信息

• Synthesis and Pharmacology of a Novel κ Opioid Receptor (KOR) Agonist with a 1,3,5-Trioxazatriquinane Skeleton
  作者：Shigeto Hirayama、Naohisa Wada、Toru Nemoto、Takashi Iwai、Hideaki Fujii、Hiroshi Nagase

  DOI：10.1021/ml5000542

  日期：2014.8.14

  We designed and synthesized the 1,3,5-trioxazatriquinane derivatives with m-hydroxyphenyl groups. These compounds include the phenethylamine structure within them, which is a common structure observed in morphinan derivatives like morphine. Among the synthesized compounds, (-)-8c with two m-hydroxyphenyl groups selectively bound and exerted full agonist activity toward the κ opioid receptor (KOR). Subcutaneously administered (-)-8c exhibited significant antinociceptive effects via the KOR in a dose-dependent manner. These results suggest the emergence of a novel class of KOR agonist.