benzyl N-[(2S)-2-[2-[2-(5-hydroxy-1H-indol-3-yl)ethylamino]-2-oxoethyl]-4-methylpentyl]carbamate | 1224700-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: benzyl N-[(2S)-2-[2-[2-(5-hydroxy-1H-indol-3-yl)ethylamino]-2-oxoethyl]-4-methylpentyl]carbamate
• CAS: 1224700-50-8
• 化学式: C₂₆H₃₃N₃O₄
• 分子量: 451.566
• InChiKey: RBUOFBQJELFGPS-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S)-2-[2-[2-(5-hydroxy-1H-indol-3-yl)ethylamino]-2-oxoethyl]-4-methylpentyl]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80%的产率得到N'-pregabalyl-serotonin
  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 、 5-羟基色胺 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56%的产率得到benzyl N-[(2S)-2-[2-[2-(5-hydroxy-1H-indol-3-yl)ethylamino]-2-oxoethyl]-4-methylpentyl]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.