去甲吗啡-6-葡糖苷酸 | 65060-95-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 中文名称: 去甲吗啡-6-葡糖苷酸
• 英文名称: Normorphine-6-glucuronide
• 英文别名: (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-hydroxy-1,2,3,4,4a,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 65060-95-9
• 化学式: C₂₂H₂₅NO₉
• 分子量: 447.442
• InChiKey: ILORZZTWORORRX-LHWQPMLGSA-N

物化性质

• 沸点：
  745.1±60.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-(2,2-dimethylpropanoyloxy)-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-tris(2-methylpropanoyloxy)oxane-2-carboxylate 在 1-氯乙基氯甲酸酯 、 甲醇 作用下， 以60%的产率得到去甲吗啡-6-葡糖苷酸
  参考文献：
  名称：

  Structure–activity relationships of some opiate glycosides

  摘要：

  A number of analogues of morphine-6-glucuronide 1 have been prepared and evaluated as potential analgesic agents by competitive mu-receptor binding assay and in vivo antinociceptive activity. The analogues show variation in the nature of the carbohydrate residue, the N-substituent, the O(3)-substituent and saturation of the 7,8-double bond compared to 1. In general, only the 6beta-glucoside or beta-glucuronide carbohydrate residues showed potent agonism; other modified carbohydrates were less active or exhibited potential antagonism. Variations in N-substituent led to either reduced agonism (N-H) or potential antagonism [N-allyl, N-(cyclopropyl)methyl]; a polar N-substituent, carboxymethyl, failed to bind. Saturation of the 7,8-double bond led to increased agonism compared to the parent compound in all three examples studied. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00056-8