纳洛酮-3,14-二乙酸酯 | 50510-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 纳洛酮-3,14-二乙酸酯
• 英文名称: naloxone 3,14-diacetate
• 英文别名: 3,14-diacetoxy-17-allyl-4,5α-epoxy-morphinan-6-one；Naloxon-3, 14-diacetat；O,O'-diacetyl-naloxone；Naloxone-3,14-diacetate；[(4R,4aS,7aR,12bS)-4a-acetyloxy-7-oxo-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] acetate
• CAS: 50510-01-5
• 化学式: C₂₃H₂₅NO₆
• 分子量: 411.455
• InChiKey: HXBIBDFSLORHLJ-HGSOSGBHSA-N

物化性质

• 溶解度：
  溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  纳洛酮-3,14-二乙酸酯 在 硫酸 作用下， 反应 24.0h， 以77%的产率得到14-Acetoxy-4,5α-epoxy-3-hydroxy-6-oxo-17-(3'-propenyl)morphinan
  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：

  纳洛酮 、 乙酸酐 反应 1.0h， 以91%的产率得到纳洛酮-3,14-二乙酸酯
  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

文献信息

• Narcotic antagonists. 1. Isomeric sulfate and acetate esters of naloxone (N-allylnoroxymorphone)
  作者：Charles Linder、Jack Fishman

  DOI：10.1021/jm00263a033

  日期：1973.5
• Narcotic antagonists. V. Stereochemistry of reactions at C-6 in 14-hydroxynoroxymorphone derivatives
  作者：Elliot F. Hahn、Jack Fishman

  DOI：10.1021/jo00889a007

  日期：1975.1