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codeine 6-β-S-D-glucose

中文名称
——
中文别名
——
英文名称
codeine 6-β-S-D-glucose
英文别名
(2S,3R,4S,5S,6R)-2-[[(4R,4aR,7R,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]sulfanyl]-6-(hydroxymethyl)oxane-3,4,5-triol
codeine 6-β-S-D-glucose化学式
CAS
——
化学式
C24H31NO7S
mdl
——
分子量
477.579
InChiKey
AMOCGWGLBOTZCQ-UAHCTOHFSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    0.3
  • 重原子数:
    33
  • 可旋转键数:
    4
  • 环数:
    6.0
  • sp3杂化的碳原子比例:
    0.67
  • 拓扑面积:
    137
  • 氢给体数:
    4
  • 氢受体数:
    9

反应信息

  • 作为产物:
    描述:
    1-硫代-b-D-葡萄糖四乙酸酯sodium hydroxide 、 sodium hydride 作用下, 以 甲醇N,N-二甲基甲酰胺 为溶剂, 反应 22.17h, 生成 codeine 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
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文献信息

  • Design, Chemical Synthesis, and Biological Evaluation of Thiosaccharide Analogues of Morphine- and Codeine-6-Glucuronide
    作者:James M. MacDougall、Xiao-Dong Zhang、Willma E. Polgar、Taline V. Khroyan、Lawrence Toll、John R. Cashman
    DOI:10.1021/jm049554t
    日期:2004.11.1
    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.
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