1-[4-[(2S)-2-[[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]amino]-3-oxo-3-phenylmethoxypropyl]phenyl]-5-oxopyrrolidine-2-carboxylic acid | 329273-74-7

• 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: 1-[4-[(2S)-2-[[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]amino]-3-oxo-3-phenylmethoxypropyl]phenyl]-5-oxopyrrolidine-2-carboxylic acid
• CAS: 329273-74-7
• 化学式: C₃₃H₃₃N₃O₇
• 分子量: 583.641
• InChiKey: GMZXYGWYYXOIGB-ZLBDCPSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[4-[(2S)-2-[[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]amino]-3-oxo-3-phenylmethoxypropyl]phenyl]-5-oxopyrrolidine-2-carboxylic acid 在 palladium on activated charcoal 氢气 作用下， 以77%的产率得到
  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 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-[4-[(2S)-2-[[(2S)-1-benzyl-5-oxopyrrolidine-2-carbonyl]amino]-3-oxo-3-phenylmethoxypropyl]phenyl]-5-oxopyrrolidine-2-carboxylic 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

文献信息

• Imide and lactam derivatives of N-benzylpyroglutamyl-l-phenylalanine as VCAM/VLA-4 antagonists
  作者：Jefferson W Tilley、Gerry Kaplan、Karen Rowan、Virginia Schwinge、Barry Wolitzky

  DOI：10.1016/s0960-894x(00)00582-5

  日期：2001.1

  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.