peracetylated 6-(3-O-acetyl)-morphinyl-α-D-mannopyranoside | 216987-53-0

• 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: peracetylated 6-(3-O-acetyl)-morphinyl-α-D-mannopyranoside
• CAS: 216987-53-0
• 化学式: C₃₃H₃₉NO₁₃
• 分子量: 657.672
• InChiKey: GSQRUKYRINQRKQ-WLGWKCLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  47.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  162.43
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  peracetylated 6-(3-O-acetyl)-morphinyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (5α,6α)-7,8-didehydro-4,5-epoxy-3-hydroxy-17-methylmorphinan-6-yl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis, Conformation, and Biological Characterization of a Sugar Derivative of Morphine that is a Potent, Long-Lasting, and Nontolerant Antinociceptive

  摘要：

  A synthetic mannoside derivative, namely, 6-morphinyl-alpha-D-mannopyranoside, shows a naloxone-reversible antinociception that is 100-fold more potent and twice as long lasting compared to morphine when administered intraperitoneally to rats in paw pressure, and tail flick tests. The compound does not produce tolerance and binds to rat mu opioid receptors with twice the affinity of morphine. NMR studies suggest that differences of activity between the derivative and its parent compound M6G might be related to their differing molecular dynamic behavior.

  DOI：

  10.1021/jm8011245
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 、 O(3)-单乙酰吗啡 在 silver trifluoromethanesulfonate 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 peracetylated 6-(3-O-acetyl)-morphinyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis, Conformation, and Biological Characterization of a Sugar Derivative of Morphine that is a Potent, Long-Lasting, and Nontolerant Antinociceptive

  摘要：

  A synthetic mannoside derivative, namely, 6-morphinyl-alpha-D-mannopyranoside, shows a naloxone-reversible antinociception that is 100-fold more potent and twice as long lasting compared to morphine when administered intraperitoneally to rats in paw pressure, and tail flick tests. The compound does not produce tolerance and binds to rat mu opioid receptors with twice the affinity of morphine. NMR studies suggest that differences of activity between the derivative and its parent compound M6G might be related to their differing molecular dynamic behavior.

  DOI：

  10.1021/jm8011245