可待因-6-葡糖苷酸 | 20736-11-2

• 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: 可待因-6-葡糖苷酸
• 英文名称: Codeine-6-glucuronide
• 英文别名: codeine 6-β-D-glucuronide；(2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 20736-11-2
• 化学式: C₂₄H₂₉NO₉
• 分子量: 475.496
• InChiKey: CRWVOYRJXPDBPM-HSCJLHHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  cystamine dihydrochioride 、 可待因-6-葡糖苷酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 C6G-cya-cya-C6G
  参考文献：
  名称：

  NOVEL MORPHINE DERIVATIVES

  摘要：

  本发明涉及新的吗啡-6-葡糖醛酸酯衍生物，其药用组合物及其用途。

  公开号：

  US20100075912A1
• 作为产物：
  描述：

  可待因 在 barium dihydroxide 、 sodium methylate 、 silver carbonate 作用下， 以 甲醇 、 苯 为溶剂， 生成 可待因-6-葡糖苷酸
  参考文献：
  名称：

  摘要：

  Purpose. The antinociceptive and immunosuppressive effects of codeine and codeine 6-glucuronide were determined in rats after intracerebroventricular administration.Methods. Codeine 6-glucuronide was synthesized using a modification of the Koenigs-Knorr reaction. A lipophilic intermediate formed during synthesis, methyl [codein-6-yl-2,3,4-tri-O-acetyl-beta-D-glucopyranosid] uronate, was also tested. Morphine was used as a positive control to compare antinociceptive potencies of these compounds.Results. All compounds tested produced significant analgesic responses, as assessed by the tail flick model. Additionally, codeine 6-glucuronide showed significantly less immunosuppressive effects than codeine in vitro.Conclusions. We conclude that codeine 6-glucuronide and related compounds may have clinical benefit in the treatment of pain in immune compromised patients.

  DOI：

  10.1023/a:1016059618633

文献信息

• Process for preparation of 4,5-Epoxymorphinan-6-oxyglucuronides
  申请人：Cenes Limited

  公开号：US20040053854A1

  公开（公告）日：2004-03-18

  Conjugation of 4,5-Epoxymorphinan-6-ols with Bromoglucuronides in the presence of Zinc containing compounds as activator under conditions capable of forming 4,5-Epoxymorphinan-6-oxyglucuronides is disclosed. This novel approach provides an efficient method for preparation of both anomers of 4,5-Epoxymorphinan-6-oxyglucuronides. The deprotected end products are useful as analgesic agents.

  在含锌化合物作为活化剂的条件下，将4,5-环氧吗啡酮-6-醇与溴葡萄糖醛酸酯共轭，形成4,5-环氧吗啡酮-6-氧基葡萄糖醛酸酯的方法被揭示。这种新颖的方法为制备4,5-环氧吗啡酮-6-氧基葡萄糖醛酸酯的两种异构体提供了高效的途径。去保护的最终产物可用作镇痛剂。
• Boldt, Petra; Rothschild, Markus A.; Kaeferstein, Herbert, Arzneimittel-Forschung/Drug Research, 2007, vol. 57, # 12, p. 787 - 794
  作者：Boldt, Petra、Rothschild, Markus A.、Kaeferstein, Herbert

  DOI：——

  日期：——
• Selective synthesis of both isomers of morphine 6-β-d-glucuronide and their analogs
  作者：Igor Rukhman、Lev Yudovich、Gennadiy Nisnevich、Arie L Gutman

  DOI：10.1016/s0040-4020(00)01080-2

  日期：2001.2

  A stereoselective synthesis of both isomers of the pharmaceutically important morphine 6-beta -D-glucuronide (M6G) and its analogs was developed. The method is based on the use of ZnBr2 for the key coupling reaction. It was shown that the alpha/beta stereoselectivity of the reaction can he directed and controlled by the amount of ZnBr2. This paper describes the synthesis, analysis and characterization of the Lu-isomer of M6C, useful as a reference marker for testing purity and stability of the morphine 6-beta -D-glucuronide (M6G). (C) 2001 Elsevier Science Ltd. All rights reserved.
• A synthesis of morphine-6-glucuronide
  作者：Christopher Lacy、Malcolm Sainsbury

  DOI：10.1016/0040-4039(95)00649-w

  日期：1995.5

  A practical synthesis of morphine-6-glucuronide from 3-acetylmorphine and methyl 2-alpha-bromo-3,4,5-tri-O-acetylglucuronate is described. Similar syntheses of codeine-6-glucuronide, codeine-6-glucoside and morphine-6-glucoside are also documented
• PROCESS FOR PREPARATION OF 4,5-EPOXYMORPHINAN-6-OXYGLUCURONIDES
  申请人：CeNes Limited

  公开号：EP1077985A1

  公开（公告）日：2001-02-28