(S)-3-(4-Amino-phenyl)-2-[((S)-1-benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-propionic acid benzyl ester | 329273-63-4

• 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: (S)-3-(4-Amino-phenyl)-2-[((S)-1-benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-propionic acid benzyl ester
• 英文别名: benzyl (2S)-3-(4-aminophenyl)-2-[[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]amino]propanoate
• CAS: 329273-63-4
• 化学式: C₂₈H₂₉N₃O₄
• 分子量: 471.556
• InChiKey: MSEBTTFSJYGGKP-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-Amino-phenyl)-2-[((S)-1-benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-propionic acid benzyl ester 在 palladium on activated charcoal 氢气 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 (2S)-2-[[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]amino]-3-[4-(2,5-dioxo-3-phenylpyrrolidin-1-yl)phenyl]propanoic acid
  参考文献：
  名称：

  Imide and lactam derivatives of N-benzylpyroglutamyl-l-phenylalanine as VCAM/VLA-4 antagonists

  摘要：

  A series of imides and lactams derived from 4-amino-N-benzylpyroglutamyl-L-phenylalanine was prepared and evaluated for activity as VCAM/VLA-4 antagonists. Imides were more potent than the corresponding lactams; several had subnanomolar IC(50)s in an ELISA based assay and were also highly effective at blocking VLA-4 expressing Ramos cell binding to VCAM coated plates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00582-5
• 作为产物：
  描述：

  N-benzyl-L-pyroglutamic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-3-(4-Amino-phenyl)-2-[((S)-1-benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-propionic acid benzyl ester
  参考文献：
  名称：

  Imide and lactam derivatives of N-benzylpyroglutamyl-l-phenylalanine as VCAM/VLA-4 antagonists

  摘要：

  A series of imides and lactams derived from 4-amino-N-benzylpyroglutamyl-L-phenylalanine was prepared and evaluated for activity as VCAM/VLA-4 antagonists. Imides were more potent than the corresponding lactams; several had subnanomolar IC(50)s in an ELISA based assay and were also highly effective at blocking VLA-4 expressing Ramos cell binding to VCAM coated plates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00582-5