N-(N-Anthranoyl)anthranoyl-DL-tryptophan ethyl ester | 296281-96-4

• 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: N-(N-Anthranoyl)anthranoyl-DL-tryptophan ethyl ester
• 英文别名: ethyl 2-[[2-[(2-aminobenzoyl)amino]benzoyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 296281-96-4
• 化学式: C₂₇H₂₆N₄O₄
• 分子量: 470.528
• InChiKey: OIGNAMQJNLXHGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(N-Anthranoyl)anthranoyl-DL-tryptophan ethyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 2-[2-(2-Amino-benzoylamino)-benzoylamino]-3-(1H-indol-3-yl)-propionic acid
  参考文献：
  名称：

  C-terminal anthranoyl–anthranilic acid derivatives and their evaluation on CCK receptors

  摘要：

  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.

  DOI：

  10.1016/s0014-827x(00)00043-4
• 作为产物：
  描述：

  靛红酸酐 在 溶剂黄146 、 三乙胺 、 锌 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 N-(N-Anthranoyl)anthranoyl-DL-tryptophan ethyl ester
  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