3-O-acetyl-6-β-S-(2',3',4',5'-tetra-O-acetyl-β-D-glucopyranosyl)morphine | 800389-00-8

• 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: 3-O-acetyl-6-β-S-(2',3',4',5'-tetra-O-acetyl-β-D-glucopyranosyl)morphine
• 英文别名: [(2R,3R,4S,5R,6S)-6-[[(4R,4aR,7R,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]sulfanyl]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 800389-00-8
• 化学式: C₃₃H₃₉NO₁₂S
• 分子量: 673.738
• InChiKey: XXIWLAROSAAJRD-OMYLCBOKSA-N

物化性质

• 熔点：
  151.9 °C(Solv: ethanol (64-17-5))
• 沸点：
  725.9±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  179
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-6-β-S-(2',3',4',5'-tetra-O-acetyl-β-D-glucopyranosyl)morphine 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以59%的产率得到morphine 6-β-S-D-glucose
  参考文献：
  名称：

  Design, Chemical Synthesis, and Biological Evaluation of Thiosaccharide Analogues of Morphine- and Codeine-6-Glucuronide

  摘要：

  A series of 6-beta-thiosaccharide analogues of morphine-6-glucuronide (M6G) and codeine-6-glucuronide (C6G) were synthesized and evaluated with the objective of preparing an analogue of M6G with improved biological activity. The affinity of the thiosaccharide analogues of M6G and C6G was examined by competitive binding assays at mu, delta, and kappa opioid receptors. The thiosaccharide compounds in the morphine series 5b, 5e, 6a, and 6c showed 1.5-2.4-fold higher affinity for the mu receptor than M6G, but were generally less selective than M6G. The functional activity of the M6G and C6G analogues was examined with the [S-35]GTP-gamma-S assay. Compounds 5b and 5e were determined to be fully mu agonists, whereas compounds 6a and 6c were partial mu agonists. The in vivo antinociceptive activity of compound 5b was evaluated by the tail flick latency test, giving an ED50 of 2.5 mg/kg.

  DOI：

  10.1021/jm049554t
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 sodium hydride 、 sodium thiomethoxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 3-O-acetyl-6-β-S-(2',3',4',5'-tetra-O-acetyl-β-D-glucopyranosyl)morphine
  参考文献：
  名称：

  Design, Chemical Synthesis, and Biological Evaluation of Thiosaccharide Analogues of Morphine- and Codeine-6-Glucuronide

  摘要：

  A series of 6-beta-thiosaccharide analogues of morphine-6-glucuronide (M6G) and codeine-6-glucuronide (C6G) were synthesized and evaluated with the objective of preparing an analogue of M6G with improved biological activity. The affinity of the thiosaccharide analogues of M6G and C6G was examined by competitive binding assays at mu, delta, and kappa opioid receptors. The thiosaccharide compounds in the morphine series 5b, 5e, 6a, and 6c showed 1.5-2.4-fold higher affinity for the mu receptor than M6G, but were generally less selective than M6G. The functional activity of the M6G and C6G analogues was examined with the [S-35]GTP-gamma-S assay. Compounds 5b and 5e were determined to be fully mu agonists, whereas compounds 6a and 6c were partial mu agonists. The in vivo antinociceptive activity of compound 5b was evaluated by the tail flick latency test, giving an ED50 of 2.5 mg/kg.

  DOI：

  10.1021/jm049554t