5,6-didehydro-4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6-carbonitrile | 342622-12-2

• 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: 5,6-didehydro-4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6-carbonitrile
• 英文别名: (1R,9R,10S)-3,10-dihydroxy-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,13-tetraene-13-carbonitrile
• CAS: 342622-12-2
• 化学式: C₁₉H₂₂N₂O₃
• 分子量: 326.395
• InChiKey: ZMCMSGKSLGXFGS-ATZDWAIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯基三甲基氯化铵 、 5,6-didehydro-4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6-carbonitrile 在 氮气 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以85%的产率得到5,6-didehydro-14β-hydroxy-3,4-dimethoxy-17-methylmorphinan-6-carbonitrile
  参考文献：
  名称：

  Effect of a 6-Cyano Substituent in 14-Oxygenated N-Methylmorphinans on Opioid Receptor Binding and Antinociceptive Potency

  摘要：

  In a continued effort to find new substitution patterns in morphinans that would produce strong antinociception while inducing lesser side effects, 4,5-oxygen bridge-opened 6-cyano-substituted N-methylmorphinans (1-3) were synthesized. All compounds showed high affinities in the low nanomolar range to the mu opioid receptor and decreased interaction with delta and kappa receptors, thus being mu selective. When tested in vivo, the 6-cyanomorphinanas acted as potent antinociceptive agents which were either more active or equipotent to their 6-keto analogues 4-6.

  DOI：

  10.1021/jm0580205
• 作为产物：
  描述：

  对甲基苯磺酰甲基异腈 、 羟可待酮 在 potassium tert-butylate 作用下， 以 乙二醇二甲醚 、 叔丁醇 为溶剂， 反应 0.5h， 以67%的产率得到5,6-didehydro-4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6-carbonitrile
  参考文献：
  名称：

  具有丙烯腈的亚型新型吗啡喃并入了亚结构，作为非氧桥联的阿片样物质配体的关键中间体。

  摘要：

  DOI：

  10.1021/ja015550r

文献信息

• Effect of a 6-Cyano Substituent in 14-Oxygenated <i>N</i>-Methylmorphinans on Opioid Receptor Binding and Antinociceptive Potency
  作者：Mariana Spetea、Elisabeth Greiner、Mario D. Aceto、Louis S. Harris、Andrew Coop、Helmut Schmidhammer

  DOI：10.1021/jm0580205

  日期：2005.7.1

  In a continued effort to find new substitution patterns in morphinans that would produce strong antinociception while inducing lesser side effects, 4,5-oxygen bridge-opened 6-cyano-substituted N-methylmorphinans (1-3) were synthesized. All compounds showed high affinities in the low nanomolar range to the mu opioid receptor and decreased interaction with delta and kappa receptors, thus being mu selective. When tested in vivo, the 6-cyanomorphinanas acted as potent antinociceptive agents which were either more active or equipotent to their 6-keto analogues 4-6.
• Novel Class of Morphinans with Acrylonitrile Incorporated Substructures as Key Intermediates for Non-Oxygen-Bridged Opioid Ligands
  作者：Elisabeth Greiner、Herwig Schottenberger、Klaus Wurst、Helmut Schmidhammer

  DOI：10.1021/ja015550r

  日期：2001.4.1