benzyl N-[(2S)-4-methyl-2-[2-oxo-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]ethyl]pentyl]carbamate | 1224700-48-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: benzyl N-[(2S)-4-methyl-2-[2-oxo-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]ethyl]pentyl]carbamate
• CAS: 1224700-48-4
• 化学式: C₂₂H₃₄N₂O₈
• 分子量: 454.521
• InChiKey: REWUDFIRMPMAIS-QVXYZCAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S)-4-methyl-2-[2-oxo-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]ethyl]pentyl]carbamate 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 乙醇 、 水 、 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到N-pregabalyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  Synthesis, characterization and in vitro pharmacology of novel pregabalin derivatives

  摘要：

  A series of novel pregabalin derivatives were synthesized starting from N-protected pregabalin, different amino sugars, adamantylamine, serotonin and tryptamine. New compounds were spectroscopically characterized and in vitro tested on gabapentin receptor binding assay. The serotonin-pregabalin adduct showed significant binding effect and its IC(50) value was determined. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.049
• 作为产物：
  描述：

  普瑞巴林杂质50 、 beta-D-吡喃葡萄糖胺 在 N-乙基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.2h， 以47%的产率得到benzyl N-[(2S)-4-methyl-2-[2-oxo-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]ethyl]pentyl]carbamate
  参考文献：
  名称：

  Synthesis, characterization and in vitro pharmacology of novel pregabalin derivatives

  摘要：

  A series of novel pregabalin derivatives were synthesized starting from N-protected pregabalin, different amino sugars, adamantylamine, serotonin and tryptamine. New compounds were spectroscopically characterized and in vitro tested on gabapentin receptor binding assay. The serotonin-pregabalin adduct showed significant binding effect and its IC(50) value was determined. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.049

文献信息

• Synthesis, characterization and in vitro pharmacology of novel pregabalin derivatives
  作者：Štefica Horvat、Zdenko Hameršak、Irena Stipetić、Thierry Jolas

  DOI：10.1016/j.ejmech.2009.12.049

  日期：2010.4

  A series of novel pregabalin derivatives were synthesized starting from N-protected pregabalin, different amino sugars, adamantylamine, serotonin and tryptamine. New compounds were spectroscopically characterized and in vitro tested on gabapentin receptor binding assay. The serotonin-pregabalin adduct showed significant binding effect and its IC(50) value was determined. (C) 2009 Elsevier Masson SAS. All rights reserved.