naloxone 3-sulfate 14-acetate ammonium salt | 51005-49-3

• 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: naloxone 3-sulfate 14-acetate ammonium salt
• 英文别名: 14-acetoxy-17-allyl-4,5α-epoxy-3-sulfooxy-morphinan-6-one; ammonium salt
• CAS: 51005-49-3
• 化学式: C₂₁H₂₃NO₈S*H₃N
• 分子量: 466.512
• InChiKey: ILSWJRYYIIZVAP-OPHZJPRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  154.44
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  naloxone 3-sulfate 14-acetate ammonium salt 在 ammonium hydroxide 、 Dowex 50 x 8 (sodium form) 作用下， 反应 2.0h， 以65%的产率得到naloxone 3-sulfate sodium salt
  参考文献：
  名称：

  Synthesis and biological activity of the phosphate and sulfate esters of naloxone and naltrexone

  摘要：

  Prodrugs of the two opiate antagonists naloxone and naltrexone, in particular the 3-monophosphate, 3-triphosphate, 9-monosulfate and 3,l4-disulfate eaters, have been synthesized and evaluated for: i) their ability to bind opioid receptors in vitro; and ii) their stability in both space and time upon entrapment into ex vivo human red blood cells (RBC). We find that, unlike the other esters, the mono- and triphosphate eaters of naloxone and naltrexone retain high (in the nmol range) affinities especially for mu- and kappa-opioid receptors. Owing to their hydrophilic nature, the two esters could possibly help in certain types of pharmacological experiments. Moreover, upon entrapment into human RBC, the triphosphate esters of naloxone and naltrexone display considerable ex vivo intracellular stability.

  DOI：

  10.1016/0223-5234(94)90125-2
• 作为产物：
  描述：

  14-Acetoxy-4,5α-epoxy-3-hydroxy-6-oxo-17-(3'-propenyl)morphinan 在 ammonium hydroxide 、 硫酸 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以63%的产率得到naloxone 3-sulfate 14-acetate ammonium salt
  参考文献：
  名称：

  Synthesis and biological activity of the phosphate and sulfate esters of naloxone and naltrexone

  摘要：

  Prodrugs of the two opiate antagonists naloxone and naltrexone, in particular the 3-monophosphate, 3-triphosphate, 9-monosulfate and 3,l4-disulfate eaters, have been synthesized and evaluated for: i) their ability to bind opioid receptors in vitro; and ii) their stability in both space and time upon entrapment into ex vivo human red blood cells (RBC). We find that, unlike the other esters, the mono- and triphosphate eaters of naloxone and naltrexone retain high (in the nmol range) affinities especially for mu- and kappa-opioid receptors. Owing to their hydrophilic nature, the two esters could possibly help in certain types of pharmacological experiments. Moreover, upon entrapment into human RBC, the triphosphate esters of naloxone and naltrexone display considerable ex vivo intracellular stability.

  DOI：

  10.1016/0223-5234(94)90125-2