methyl (2S)-2-[[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]amino]-3-[4-(piperazine-1-carbonyl)phenyl]propanoate | 412353-01-6

• 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: methyl (2S)-2-[[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]amino]-3-[4-(piperazine-1-carbonyl)phenyl]propanoate
• CAS: 412353-01-6
• 化学式: C₂₇H₃₂N₄O₅
• 分子量: 492.575
• InChiKey: CAEICZQZUPVEFS-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]amino]-3-[4-(piperazine-1-carbonyl)phenyl]propanoate 在 sodium hydroxide 、 乙醇 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 生成 (S)-2-[((S)-1-Benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-3-{4-[4-(3-hydroxy-benzoyl)-piperazine-1-carbonyl]-phenyl}-propionic acid
  参考文献：
  名称：

  N-Acyl-l-phenylalanine derivatives as potent VLA-4 antagonists that mimic a cyclic peptide conformation

  摘要：

  A series of N-benzylpyroglutamyl-L-phenylalanine derivatives bearing carbamoyl substituents in the 3- or 4-positions was prepared and assayed for inhibition of the interaction between VCAM and VLA-4. Potent inhibition was observed in a number of analogues with substitution in the 4-position favored over the 3-position. A crystal structure of the key intermediate 25 indicates that it accesses a low energy conformation which closely matches key pharmacophores of a structurally characterized cyclic peptide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00711-9
• 作为产物：
  描述：

  N-benzyl-L-pyroglutamic acid 在 盐酸 、 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 methyl (2S)-2-[[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]amino]-3-[4-(piperazine-1-carbonyl)phenyl]propanoate
  参考文献：
  名称：

  N-Acyl-l-phenylalanine derivatives as potent VLA-4 antagonists that mimic a cyclic peptide conformation

  摘要：

  A series of N-benzylpyroglutamyl-L-phenylalanine derivatives bearing carbamoyl substituents in the 3- or 4-positions was prepared and assayed for inhibition of the interaction between VCAM and VLA-4. Potent inhibition was observed in a number of analogues with substitution in the 4-position favored over the 3-position. A crystal structure of the key intermediate 25 indicates that it accesses a low energy conformation which closely matches key pharmacophores of a structurally characterized cyclic peptide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00711-9

文献信息

• N-Acyl-l-phenylalanine derivatives as potent VLA-4 antagonists that mimic a cyclic peptide conformation
  作者：Li Chen、Jefferson Tilley、Richard V. Trilles、Weiya Yun、David Fry、Charles Cook、Karen Rowan、Virginia Schwinge、Robert Campbell

  DOI：10.1016/s0960-894x(01)00711-9

  日期：2002.1

  A series of N-benzylpyroglutamyl-L-phenylalanine derivatives bearing carbamoyl substituents in the 3- or 4-positions was prepared and assayed for inhibition of the interaction between VCAM and VLA-4. Potent inhibition was observed in a number of analogues with substitution in the 4-position favored over the 3-position. A crystal structure of the key intermediate 25 indicates that it accesses a low energy conformation which closely matches key pharmacophores of a structurally characterized cyclic peptide. (C) 2002 Elsevier Science Ltd. All rights reserved.