2-(RS)-3-(4-hydroxyphenyl)-2-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}propionic acid | 1155261-76-9

• 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: 2-(RS)-3-(4-hydroxyphenyl)-2-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}propionic acid
• 英文别名: (2R,S)-3-(4-Hydroxy-phenyl)-2-{2-[(1H-indole-2-carbonyl)-amino]-benzoylamino}-propionic acid；3-(4-hydroxyphenyl)-2-[[2-(1H-indole-2-carbonylamino)benzoyl]amino]propanoic acid
• CAS: 1155261-76-9
• 化学式: C₂₅H₂₁N₃O₅
• 分子量: 443.459
• InChiKey: RKRFSLGRJVQJPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  132
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2RS)-3-(4-benzyloxyphenyl)-2-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}propionic acid benzyl ester 在 palladium 10% on activated carbon 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以43%的产率得到2-(RS)-3-(4-hydroxyphenyl)-2-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}propionic acid
  参考文献：
  名称：

  Anthranilic acid based CCK1 receptor antagonists: Blocking the receptor with the same ‘words’ of the endogenous ligand

  摘要：

  The anthranilic acid diamides represent the more recent class of nonpeptide CCK1 receptor antagonists. This class is characterized by the presence of anthranilic acid, used as a molecular scaffold, and two pharmacophores selected from the C-terminal tetrapeptide of CCK. The lead compound coded VL-0395, endowed with sub-micromolar affinity towards CCK1 receptors, was characterized by the presence of Phe and 2-indole moiety at the C- and N-termini of anthranilic acid, respectively. Herein we describe the first step of the anthranilic acid C- terminal optimization using, instead of Phe, aminoacids belonging to the primary structure of CCK-8 and other not coded residues. Thus we demonstrate that the CCK1 receptor affinity depends on the nature of the aminoacidic side chain as well as that the free carboxy group of the alpha-aminoacids is crucial for the binding. The R enantiomers of the most active compounds represent the eutomers of this class of antagonists confirming thus the stereo preference of the receptor. Moreover this SAR study demonstrates that the receptor binding pocket, that host the aminoacidic side chain, results much more tolerant respect to that accommodating the indole ring. As a result, an appropriate variation of the aminoacidic side chain could provide a better CCK1 receptor affinity diorthosis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.012