(S)-2-[((S)-1-Benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-3-[3-(piperazine-1-carbonyl)-phenyl]-propionic acid methyl ester | 412353-13-0

• 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: (S)-2-[((S)-1-Benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-3-[3-(piperazine-1-carbonyl)-phenyl]-propionic acid methyl ester
• CAS: 412353-13-0
• 化学式: C₂₇H₃₂N₄O₅
• 分子量: 492.575
• InChiKey: CNSLKKKXVUTOGD-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108.05
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[((S)-1-Benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-3-[3-(piperazine-1-carbonyl)-phenyl]-propionic acid methyl ester 在 sodium hydroxide 、 乙醇 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 生成 (S)-3-[3-(4-Benzoyl-piperazine-1-carbonyl)-phenyl]-2-[((S)-1-benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-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：

  1,3-苯二甲醇 在 palladium on activated charcoal 盐酸 、 manganese(IV) oxide 、 jones reagent 、 氢氟酸 、 氢气 、 sodium hydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 四甲基胍 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 生成 (S)-2-[((S)-1-Benzyl-5-oxo-pyrrolidine-2-carbonyl)-amino]-3-[3-(piperazine-1-carbonyl)-phenyl]-propionic acid methyl ester
  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