2-(RS)-(2-aminobenzoylamino)-3-(1H-indol-3-yl)propionic acid ethyl ester | 296282-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(RS)-(2-aminobenzoylamino)-3-(1H-indol-3-yl)propionic acid ethyl ester
• 英文别名: N-Anthranoyl-DL-tryptophan ethyl ester
• CAS: 296282-20-7
• 化学式: C₂₀H₂₁N₃O₃
• 分子量: 351.405
• InChiKey: FUTVJEAJCYZMPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  97.21
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(RS)-(2-aminobenzoylamino)-3-(1H-indol-3-yl)propionic acid ethyl ester 在 溶剂黄146 、 三乙胺 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis of new anthranilic acid dimer derivatives and their evaluation on CCK receptors

  摘要：

  We have described previously an innovative bond disconnection strategy of asperlicin, a naturally occurring CCK receptor antagonist, leading to anthranilic acid dimer and tryptophan synthons. We have also demonstrated that when the tryptophan residue is connected to the C- or N-terminal sides of the anthranilic acid dimer, compounds with similar micromolar CCK-A receptor affinities are obtained. In order to investigate the binding effects of different N-terminal substitution, in this paper we describe a new series of anthranilic acid dimer derivatives, characterized by the presence of the tryptophan residue in the C-terminus of the dimer. Among the compounds synthesized, the N-1H-indol-3-propionyl derivative exhibited an improved, at the micromolar range, affinity for the CCK-A receptor in comparison to that of either, the N-unsubstituted derivative and asperlicin. The lead compound emerging from this key step of our investigation represents the new starting point for the development of a new class of CCK-A receptor ligands. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00053-7
• 作为产物：
  描述：

  靛红酸酐 、 DL-色氨酸乙酯盐酸盐 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以81%的产率得到2-(RS)-(2-aminobenzoylamino)-3-(1H-indol-3-yl)propionic acid ethyl ester
  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

文献信息

• C-terminal anthranoyl–anthranilic acid derivatives and their evaluation on CCK receptors
  作者：Antonio Varnavas、Lucia Lassiani、Elena Luxich、Valentina Valenta

  DOI：10.1016/s0014-827x(00)00043-4

  日期：2000.4

  A series of C-terminal anthranoyl-anthranilic acid derivatives arising from a strict bond disconnection approach of asperlicin were synthesized and examined for their CCK receptor affinities. These compounds represent the second step of our investigation directed toward the search for alternative substructures of asperlicin as a starting point for the development of a new class of CCK ligands. The obtained micromolar affinities for CCK-A rather than CCK-B receptor confirm that the anthranilic acid dimer represents a useful template for the development of selective CCK-A receptor ligands. (C) 2000 Elsevier Science S.A. All rights reserved.