3-phenyl-2(RS)-{2-[(4,5,6,7-tetrahydro-1H-indole-2-carbonyl)-amino]-benzoylamino}-propionic acid ethyl ester | 685142-01-2

• 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: 3-phenyl-2(RS)-{2-[(4,5,6,7-tetrahydro-1H-indole-2-carbonyl)-amino]-benzoylamino}-propionic acid ethyl ester
• CAS: 685142-01-2
• 化学式: C₂₇H₂₉N₃O₄
• 分子量: 459.545
• InChiKey: DHSZBROVLJASDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  100.29
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-2(RS)-{2-[(4,5,6,7-tetrahydro-1H-indole-2-carbonyl)-amino]-benzoylamino}-propionic acid ethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以78%的产率得到3-phenyl-2(RS)-{2-[(4,5,6,7-tetrahydro-1H-indole-2-carbonyl)-amino]-benzoylamino}-propionic acid
  参考文献：
  名称：

  Anthranilic acid based CCK1 antagonists: the 2-indole moiety may represent a “needle” according to the recent homonymous concept

  摘要：

  Recently we described an innovative class of non-peptide CCK1 antagonists keeping appropriate pharmacophoric groups on the anthranilic acid employed as a molecular scaffold. The lead compound obtained, VL-0395, characterized by the presence of Phe and the 2-indole moiety at the C- and N-termini of anthranilic acid, respectively, is endowed with submicromolar affinity towards CCK1 receptors. Thus, we have prepared and tested on CCK receptors a library of VL-0395 analogues in order to investigate the precise topological and essential key interactions of the 2-indole group of the lead with the CCK1 receptor. The obtained results confirm that this group establishes very specific interactions with this receptor sub-site and may be viewed as a "needle" group. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.11.010
• 作为产物：
  描述：

  4,5,6,7-四氢-1H-吲哚-2-羧酸乙酯 在 吡啶 、 lithium hydroxide 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 水 为溶剂， 反应 19.0h， 生成 3-phenyl-2(RS)-{2-[(4,5,6,7-tetrahydro-1H-indole-2-carbonyl)-amino]-benzoylamino}-propionic acid ethyl ester
  参考文献：
  名称：

  Anthranilic acid based CCK1 antagonists: the 2-indole moiety may represent a “needle” according to the recent homonymous concept

  摘要：

  Recently we described an innovative class of non-peptide CCK1 antagonists keeping appropriate pharmacophoric groups on the anthranilic acid employed as a molecular scaffold. The lead compound obtained, VL-0395, characterized by the presence of Phe and the 2-indole moiety at the C- and N-termini of anthranilic acid, respectively, is endowed with submicromolar affinity towards CCK1 receptors. Thus, we have prepared and tested on CCK receptors a library of VL-0395 analogues in order to investigate the precise topological and essential key interactions of the 2-indole group of the lead with the CCK1 receptor. The obtained results confirm that this group establishes very specific interactions with this receptor sub-site and may be viewed as a "needle" group. (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.11.010