syn,anti-naltrexonazine

• 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: syn,anti-naltrexonazine
• 化学式: C₄₀H₄₆N₄O₆
• 分子量: 678.828
• InChiKey: GSYDZKZBXPTRGD-OQDCYLFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  50.0
• 可旋转键数：
  5.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  130.58
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  纳曲酮 在 肼 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 naltrexone azine 、 syn,anti-naltrexonazine
  参考文献：
  名称：

  X-ray crystal structure of the opioid ligand naltrexonazine

  摘要：

  The anti-anti isomer of naltrexonazine (1) was synthesized, and its configuration was confirmed by X-ray crystallography. The syn-anti isomer is readily converted to 1 under acidic conditions. The apparent equal receptor binding of 1 and syn-anti isomer indicates that isomerization of the azine moiety may take place under the conditions of biological evaluation. Two possible explanations for wash-resistant binding of 1 to opioid receptors are presented. The first possibility involves a noncovalent interaction of the ligand with the opioid receptor, and the second considers covalent binding by a receptor-based sulfhydryl group.

  DOI：

  10.1021/jm00391a035

文献信息

• X-ray crystal structure of the opioid ligand naltrexonazine
  作者：Z. Urbanczyk-Lipkowska、A. W. Lipkowski、M. C. Etter、E. F. Hahn、G. W. Pasternak、P. S. Portoghese

  DOI：10.1021/jm00391a035

  日期：1987.8

  The anti-anti isomer of naltrexonazine (1) was synthesized, and its configuration was confirmed by X-ray crystallography. The syn-anti isomer is readily converted to 1 under acidic conditions. The apparent equal receptor binding of 1 and syn-anti isomer indicates that isomerization of the azine moiety may take place under the conditions of biological evaluation. Two possible explanations for wash-resistant binding of 1 to opioid receptors are presented. The first possibility involves a noncovalent interaction of the ligand with the opioid receptor, and the second considers covalent binding by a receptor-based sulfhydryl group.