N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-glycine benzyl ester | 76314-34-6

• 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: N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-glycine benzyl ester
• 英文别名: benzyl 2-[[(2S)-1-[2-(phenylmethoxycarbonylamino)acetyl]pyrrolidine-2-carbonyl]amino]acetate
• CAS: 76314-34-6
• 化学式: C₂₄H₂₇N₃O₆
• 分子量: 453.495
• InChiKey: VSVNWLLQCDHQGT-FQEVSTJZSA-N

物化性质

• 沸点：
  710.8±60.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  114.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-glycine benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以85%的产率得到甘氨酰-L-脯氨酰-甘氨酸
  参考文献：
  名称：

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

  摘要：

  The synthesis of eight GPE* analogues, wherein the gamma-carboxylic moiety of the glutamic residue has been modified, is described by coupling readily accessible N-benzyloxycarbonyl-glycyl-L-proline with various analogues of glutamic acid. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glutamate residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.006
• 作为产物：
  描述：

  Z-甘氨酸-脯氨酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.75h， 生成 N-[N-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-glycine benzyl ester
  参考文献：
  名称：

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

  摘要：

  The synthesis of eight GPE* analogues, wherein the gamma-carboxylic moiety of the glutamic residue has been modified, is described by coupling readily accessible N-benzyloxycarbonyl-glycyl-L-proline with various analogues of glutamic acid. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glutamate residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.10.006

文献信息

• Synthesis and pharmacological evaluation of side chain modified glutamic acid analogues of the neuroprotective agent glycyl-l-prolyl-l-glutamic acid (GPE)
  作者：Margaret A. Brimble、Nicholas S. Trotter、Paul W.R. Harris、Frank Sieg

  DOI：10.1016/j.bmc.2004.10.006

  日期：2005.1

  The synthesis of eight GPE* analogues, wherein the gamma-carboxylic moiety of the glutamic residue has been modified, is described by coupling readily accessible N-benzyloxycarbonyl-glycyl-L-proline with various analogues of glutamic acid. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glutamate residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.