(2R,3S,4R,5R,6R)-5-amino-6-(2-azidoethoxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol hydrochloride | 1354506-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-5-amino-6-(2-azidoethoxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol hydrochloride
• CAS: 1354506-53-8
• 化学式: C₈H₁₆N₄O₅*ClH
• 分子量: 284.7
• InChiKey: BMDIWUFHVXBCBV-TVLNMICESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  153.93
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-5-amino-6-(2-azidoethoxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol hydrochloride 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Prednisolone succinate–glucosamine conjugate: Synthesis, characterization and in vitro cellular uptake by kidney cell lines

  摘要：

  Prednisolone succinate glucosamine (PSG) conjugate, a prodrug for prednisolone, was synthesized and confirmed by NMR and MS spectrum. The stabilities of the prodrug in PBS (pH 2.50, 5.00, 7.20, and 7.89) were studied. Cytotoxicity and uptake assay of the prodrug were perfomed on HK-2 and MDCK cell lines. The results showed that compared with prednisolone, the PSG not only did not increase the cytotoxicity but also improved the uptake to 2.2 times of prednisolone by the cells. Thus, it indicated that glucosamine might be a potential carrier for kidney-targeting delivery of prednisolone. (C) 2011 Zhi Rong Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.07.023
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (2R,3S,4R,5R,6R)-5-amino-6-(2-azidoethoxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol hydrochloride
  参考文献：
  名称：

  Prednisolone succinate–glucosamine conjugate: Synthesis, characterization and in vitro cellular uptake by kidney cell lines

  摘要：

  Prednisolone succinate glucosamine (PSG) conjugate, a prodrug for prednisolone, was synthesized and confirmed by NMR and MS spectrum. The stabilities of the prodrug in PBS (pH 2.50, 5.00, 7.20, and 7.89) were studied. Cytotoxicity and uptake assay of the prodrug were perfomed on HK-2 and MDCK cell lines. The results showed that compared with prednisolone, the PSG not only did not increase the cytotoxicity but also improved the uptake to 2.2 times of prednisolone by the cells. Thus, it indicated that glucosamine might be a potential carrier for kidney-targeting delivery of prednisolone. (C) 2011 Zhi Rong Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.07.023