6,7-didehydro-4,14-hydroxy-3-methoxy-17-methyl-6,7:2',3'-indolomorphinan

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 6,7-didehydro-4,14-hydroxy-3-methoxy-17-methyl-6,7:2',3'-indolomorphinan
• 英文别名: (1R,13S,14R)-19-methoxy-24-methyl-4,24-diazahexacyclo[12.7.3.01,13.03,11.05,10.016,21]tetracosa-3(11),5,7,9,16(21),17,19-heptaene-13,20-diol
• 化学式: C₂₄H₂₆N₂O₃
• 分子量: 390.482
• InChiKey: NVKFKYFEFLFZKJ-AGILITTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  盐酸羟可待酮 在 盐酸 、 对甲苯磺酸 、 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 反应 2.17h， 生成 6,7-didehydro-4,14-hydroxy-3-methoxy-17-methyl-6,7:2',3'-indolomorphinan
  参考文献：
  名称：

  δ Opioid Affinity and Selectivity of 4-Hydroxy-3-methoxyindolomorphinan Analogues Related to Naltrindole

  摘要：

  To investigate the effect of the introduction of a 4-phenolic substituent on the delta opioid affinity and selectivity of the indolomorphinans, a range of 4-phenolic analogues of naltrindole were prepared and evaluated in in vitro assays. Although the majority of the ligands displayed poor affinity for all three opioid receptors (mu, kappa, delta), 17-cyclopropylmethyl-6,7-didehydro-4-hydroxy-3-methoxy-6,7:2',3'-indolomorphinan (13) was an exception, displaying excellent delta binding selectivity (delta K-i = 7 nM, mu/delta = 1900, mu/kappa = 1130). GTP-gamma-S functional assays showed 13 to be a selective delta antagonist, albeit with lower potency than naltrindole. Although the reason for the unique profile of 13 could not be determined, these results validate our approach of introducing groups into the indolomorphinans that are known to reduce mu activity, to obtain increased delta selectivity.

  DOI：

  10.1021/jm9807003

文献信息

• Studies into the Direct Conversion of Indolomorphinans to their 4-Phenolic Derivatives
  作者：Dean Y Maeda、Andrew Coop

  DOI：10.1016/s0040-4020(00)00667-0

  日期：2000.9

  A one step method to convert 3-O-methyl substituted indolomorphinans into their 4-phenolic derivatives through reductive opening of the 4,5-bridge is described.

  描述了通过还原性打开4，5-桥将3- O-甲基取代的吲哚吗啡喃转化为其4-酚衍生物的一步方法。