10-hydroxynaltrexone 3-methyl ether | 96445-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 10-hydroxynaltrexone 3-methyl ether
• 英文别名: (4R,4aS,7aR,12bS,13S)-3-(cyclopropylmethyl)-4a,13-dihydroxy-9-methoxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 96445-12-4
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: JAERZOFTLPSTBG-DARKYYSBSA-N

物化性质

• 沸点：
  596.3±50.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)
• 溶解度：
  溶于丙酮、二氯甲烷、DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  10-hydroxynaltrexone 3-methyl ether 在 CrO₃-DMP 、 三溴化硼 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 43.25h， 生成 10-酮基纳曲酮
  参考文献：
  名称：

  10-Ketonaltrexone and 10-ketooxymorphone

  摘要：

  Ethylketocyclazocine (1) has greater kappa/mu selectivity than cyclazocine in brain binding assays. 10-Ketonaltrexone (11) and 10-ketooxymorphone (10) were prepared from naltrexone 3-methyl ether and oxycodone, respectively. Bioassays in the myenteric plexus longitudinal muscle preparation of the guinea pig ileum and in the mouse vas deferens, in addition to brain binding assays, demonstrated that 10 and 11 were far less potent than naltrexone (2) and oxymorphone (3) at mu sites and also had little affinity for kappa and delta sites. It is concluded that introduction of the 10-keto group in naltrexone and oxymorphone diminished opioid effects at all binding sites.

  DOI：

  10.1021/jm00145a024
• 作为产物：
  描述：

  纳曲酮EP杂质J 在 chromium(VI) oxide 、 硫酸 作用下， 反应 28.0h， 以2.3%的产率得到纳曲酮杂质
  参考文献：
  名称：

  10-Ketonaltrexone and 10-ketooxymorphone

  摘要：

  Ethylketocyclazocine (1) has greater kappa/mu selectivity than cyclazocine in brain binding assays. 10-Ketonaltrexone (11) and 10-ketooxymorphone (10) were prepared from naltrexone 3-methyl ether and oxycodone, respectively. Bioassays in the myenteric plexus longitudinal muscle preparation of the guinea pig ileum and in the mouse vas deferens, in addition to brain binding assays, demonstrated that 10 and 11 were far less potent than naltrexone (2) and oxymorphone (3) at mu sites and also had little affinity for kappa and delta sites. It is concluded that introduction of the 10-keto group in naltrexone and oxymorphone diminished opioid effects at all binding sites.

  DOI：

  10.1021/jm00145a024