(S)-1-{2-[4-(3-o-Tolyl-ureido)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid | 819078-82-5

• 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)-1-{2-[4-(3-o-Tolyl-ureido)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid
• 英文别名: (2S)-1-[2-[4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]pyrrolidine-2-carboxylic acid
• CAS: 819078-82-5
• 化学式: C₂₁H₂₃N₃O₄
• 分子量: 381.431
• InChiKey: DEVYFNMZQRNBON-SFHVURJKSA-N

物化性质

• 沸点：
  551.2±50.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  98.74
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-1-{2-[4-(3-o-Tolyl-ureido)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 、 甲醇 为溶剂， 生成 4-[((S)-1-{2-[4-(3-o-Tolyl-ureido)-phenyl]-acetyl}-pyrrolidine-2-carbonyl)-amino]-butyric acid
  参考文献：
  名称：

  Identified a morpholinyl-4-piperidinylacetic acid derivative as a potent oral active VLA-4 antagonist

  摘要：

  An investigation into the structure-activity relationship of a lead compound, prolyl-5-aminopentanoic acid 4, led to the identification of a novel series of 4-piperidinylacetic acid, 1-piperazinylacetic acid, and 4-aminobenzoic acid derivatives as potent VLA-4 antagonists with low nanomolar IC50 values. A representative compound morpholinyl-4-piperidinylacetic acid derivative (13d: IC50 = 4.4nM) showed efficacy in the Ascaris-antigen sensitized murine airway inflammation model by oral administration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.041
• 作为产物：
  描述：

  (S)-1-{2-[4-(3-o-Tolyl-ureido)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-1-{2-[4-(3-o-Tolyl-ureido)-phenyl]-acetyl}-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Identified a morpholinyl-4-piperidinylacetic acid derivative as a potent oral active VLA-4 antagonist

  摘要：

  An investigation into the structure-activity relationship of a lead compound, prolyl-5-aminopentanoic acid 4, led to the identification of a novel series of 4-piperidinylacetic acid, 1-piperazinylacetic acid, and 4-aminobenzoic acid derivatives as potent VLA-4 antagonists with low nanomolar IC50 values. A representative compound morpholinyl-4-piperidinylacetic acid derivative (13d: IC50 = 4.4nM) showed efficacy in the Ascaris-antigen sensitized murine airway inflammation model by oral administration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.041