phenyl-1,4-bis[carbonyl-N-(L-proline)] | 473797-75-0

• 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: phenyl-1,4-bis[carbonyl-N-(L-proline)]
• 英文别名: (2S)-1-[4-[(2S)-2-carboxypyrrolidine-1-carbonyl]benzoyl]pyrrolidine-2-carboxylic acid
• CAS: 473797-75-0
• 化学式: C₁₈H₂₀N₂O₆
• 分子量: 360.367
• InChiKey: OSXYNPAKEAJIEK-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl-1,4-bis[carbonyl-N-(L-proline)] 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 {4-[(S)-2-(Pyrrolidine-1-carbonyl)-pyrrolidine-1-carbonyl]-phenyl}-[(S)-2-(pyrrolidine-1-carbonyl)-pyrrolidin-1-yl]-methanone
  参考文献：
  名称：

  Dicarboxylic Acid bis(l-Prolyl-pyrrolidine) Amides as Prolyl Oligopeptidase Inhibitors

  摘要：

  New dicarboxylic acid bis(L-prolyl-pyrrolidine) amides were synthesized, and their inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. As compared with earlier described prolyl oligopeptidase inhibitors, these new compounds have in common an L-prolyl-pyrrolidine moiety, but the typical lipophilic acyl end group is replaced by another L-prolyl-pyrrolidine moiety connected symmetrically with a short dicarboxylic acid linker. These compounds are a new type of peptidomimetic prolyl oligopeptidase inhibitor.

  DOI：

  10.1021/jm020966g
• 作为产物：
  描述：

  对苯二甲酰氯 、 L-脯氨酸 在 sodium hydroxide 作用下， 以 乙醚 为溶剂， 生成 phenyl-1,4-bis[carbonyl-N-(L-proline)]
  参考文献：
  名称：

  Dicarboxylic Acid bis(l-Prolyl-pyrrolidine) Amides as Prolyl Oligopeptidase Inhibitors

  摘要：

  New dicarboxylic acid bis(L-prolyl-pyrrolidine) amides were synthesized, and their inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. As compared with earlier described prolyl oligopeptidase inhibitors, these new compounds have in common an L-prolyl-pyrrolidine moiety, but the typical lipophilic acyl end group is replaced by another L-prolyl-pyrrolidine moiety connected symmetrically with a short dicarboxylic acid linker. These compounds are a new type of peptidomimetic prolyl oligopeptidase inhibitor.

  DOI：

  10.1021/jm020966g

文献信息

• Homochiral Metal–Organic Frameworks with Tunable Nanoscale Channel Array and Their Enantioseparation Performance against Chiral Diols
  作者：Chao Zhuo、Yuehong Wen、Shengmin Hu、Tianlu Sheng、Ruibiao Fu、Zhenzhen Xue、Hao Zhang、Haoran Li、Jigang Yuan、Xi Chen、Xintao Wu

  DOI：10.1021/acs.inorgchem.7b00352

  日期：2017.6.5

  Enantioseparation is an integral process hi the phatthaceutical industry, considering the ever-increasing demand for chiral medicthe products. As a new material, porous metal-organic frameworks (MOFs) have shown their potential application in this field=becaue their structures are easy to adjust and control. Though chiral recognition between racemic substrates and frameworks has made preliminary progress, discusSions of their size-matching effects are rare. Herein with the help of channel-tunable homochiral MOFs (HMOFs), dials of different sizes have been separated in good enantiomeric excess (ee%). In addition,,the ee% reaches 67.4% for the first tithe for dials as large as 1,1,2-tripheny1-1,2-ethanediol, which turns out to be the most effective value so far.
• Dicarboxylic Acid <i>bis</i>(<scp>l</scp>-Prolyl-pyrrolidine) Amides as Prolyl Oligopeptidase Inhibitors
  作者：Erik A. A. Wallén、Johannes A. M. Christiaans、Markus M. Forsberg、Jarkko I. Venäläinen、Pekka T. Männistö、Jukka Gynther

  DOI：10.1021/jm020966g

  日期：2002.9.1

  New dicarboxylic acid bis(L-prolyl-pyrrolidine) amides were synthesized, and their inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. As compared with earlier described prolyl oligopeptidase inhibitors, these new compounds have in common an L-prolyl-pyrrolidine moiety, but the typical lipophilic acyl end group is replaced by another L-prolyl-pyrrolidine moiety connected symmetrically with a short dicarboxylic acid linker. These compounds are a new type of peptidomimetic prolyl oligopeptidase inhibitor.