dibenzyl N-benzyloxycarbonyl-aminoisobutyryl-L-prolyl-L-glutamate | 842120-64-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dibenzyl N-benzyloxycarbonyl-aminoisobutyryl-L-prolyl-L-glutamate
• 英文别名: dibenzyl-N-benzyloxycarbonyl aminoisobutyryl-L-prolyl-L-glutamate；Cbz-Aib-Pro-Glu(OBn)-OBn；dibenzyl (2S)-2-[[(2S)-1-[2-methyl-2-(phenylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carbonyl]amino]pentanedioate
• CAS: 842120-64-3
• 化学式: C₃₆H₄₁N₃O₈
• 分子量: 643.737
• InChiKey: DRIIUBBMVIJHOQ-KYJUHHDHSA-N

物化性质

• 沸点：
  830.2±65.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dibenzyl N-benzyloxycarbonyl-aminoisobutyryl-L-prolyl-L-glutamate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以52%的产率得到aminoisobutyryl-L-prolyl-L-glutamic acid hydrochloride
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of glycine-modified analogues of the neuroprotective agent glycyl-l-prolyl-l-glutamic acid (GPE)

  摘要：

  The synthesis of 10 G*PE analogues, wherein the glycine residue has been modified, is described by coupling readily accessible dibenzyl-L-prolyl-L-glutamate 2 with various analogues of glycine. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glycine residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.004
• 作为产物：
  描述：

  N-苄氧羰酰基-2-甲基丙氨酸 在 sodium hydroxide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 43.0h， 生成 dibenzyl N-benzyloxycarbonyl-aminoisobutyryl-L-prolyl-L-glutamate
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of glycine-modified analogues of the neuroprotective agent glycyl-l-prolyl-l-glutamic acid (GPE)

  摘要：

  The synthesis of 10 G*PE analogues, wherein the glycine residue has been modified, is described by coupling readily accessible dibenzyl-L-prolyl-L-glutamate 2 with various analogues of glycine. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glycine residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.004

文献信息

• Analogs of Glycyl-Prolyl-Glutamate
  申请人：Brimble Margaret Anne

  公开号：US20080145335A1

  公开（公告）日：2008-06-19

  Embodiments of this invention include novel analogs of Glycyl-Prolyl-Glutamate (GPE) and compositions containing such analogs of GPE. Of these, certain analogs have modified proline residues. Other embodiments of this invention include uses of analogs of GPE to protect neural cells from degeneration and/or death in response to injury or disease. Disorders treatable with compounds and compositions of this invention include hypoxia/ischemia, toxic injury, and chronic neurodegenerative disorders including Parkinson's disease.

  本发明的实施例包括甘氨酰-脯氨酰-谷氨酸（GPE）的新型类似物和含有这种类似物的组合物。其中，某些类似物具有改性脯氨酸残基。本发明的其他实施例包括使用GPE的类似物保护神经细胞免受损伤或疾病引起的退化和/或死亡。可用本发明的化合物和组合物治疗的疾病包括缺氧/缺血、毒性损伤和慢性神经退行性疾病，包括帕金森病。
• WO2006/127702
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and pharmacological evaluation of glycine-modified analogues of the neuroprotective agent glycyl-l-prolyl-l-glutamic acid (GPE)
  作者：Michelle Y.H. Lai、Margaret A. Brimble、David J. Callis、Paul W.R. Harris、Mark S. Levi、Frank Sieg

  DOI：10.1016/j.bmc.2004.10.004

  日期：2005.1

  The synthesis of 10 G*PE analogues, wherein the glycine residue has been modified, is described by coupling readily accessible dibenzyl-L-prolyl-L-glutamate 2 with various analogues of glycine. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glycine residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.