N-(N-anthranoyl) anthranoyl-DL-phenylalanine ethyl ester | 296281-97-5

• 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: N-(N-anthranoyl) anthranoyl-DL-phenylalanine ethyl ester
• 英文别名: Ethyl 2-[[2-[(2-aminobenzoyl)amino]benzoyl]amino]-3-phenylpropanoate
• CAS: 296281-97-5
• 化学式: C₂₅H₂₅N₃O₄
• 分子量: 431.491
• InChiKey: WDTRAJBNCFGBLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(N-anthranoyl) anthranoyl-DL-phenylalanine ethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 生成 2-amino-N-[2-[(1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl]phenyl]benzamide
  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：

  (2S)-2-氨基-3-苯基丙酸乙酯 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-phenylalanine ethyl ester
  参考文献：
  名称：

  Synthesis of N-terminal substituted anthranilic acid dimer derivatives for evaluation on CCK receptors

  摘要：

  A series of new N-substituted anthranilic acid dimer derivatives having a C-terminal Phe residue was synthesized,and evaluated for their affinity for CCK receptors. These compounds resulted from a blended approach based firstly on the use of an alternative substructure embedded within asperlicin and secondly on the derivatization of this template with substituents chosen considering the C-terminal primary structure of the endogenous ligand. Although these compounds exhibited a regnylogical-type organization similar to that of CCK-4, they are characterized by about 1000-fold greater affinity for CCK-A receptor than the C-terminal tetrapeptide. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01071-0

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.
• Synthesis of N-terminal substituted anthranilic acid dimer derivatives for evaluation on CCK receptors
  作者：Antonio Varnavas、Valentina Valenta、Federico Berti、Lucia Lassiani

  DOI：10.1016/s0014-827x(01)01071-0

  日期：2001.8

  A series of new N-substituted anthranilic acid dimer derivatives having a C-terminal Phe residue was synthesized,and evaluated for their affinity for CCK receptors. These compounds resulted from a blended approach based firstly on the use of an alternative substructure embedded within asperlicin and secondly on the derivatization of this template with substituents chosen considering the C-terminal primary structure of the endogenous ligand. Although these compounds exhibited a regnylogical-type organization similar to that of CCK-4, they are characterized by about 1000-fold greater affinity for CCK-A receptor than the C-terminal tetrapeptide. (C) 2001 Elsevier Science S.A. All rights reserved.