(RS)-(2-aminobenzoylamino)phenyl acetic acid ethyl ester | 296282-22-9

• 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: (RS)-(2-aminobenzoylamino)phenyl acetic acid ethyl ester
• CAS: 296282-22-9
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: HQNVWWYHMTWMJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.42
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (RS)-(2-aminobenzoylamino)phenyl acetic 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 3.0h， 生成 Ethyl 2-[[2-[(2-aminobenzoyl)amino]benzoyl]amino]-2-phenylacetate
  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 、 Α-氨基-2-苯乙酸乙酯盐酸盐 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以42%的产率得到(RS)-(2-aminobenzoylamino)phenyl acetic acid ethyl ester
  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

文献信息

• New Anthranilic Acid Based Antagonists with High Affinity and Selectivity for the Human Cholecystokinin Receptor 1 (hCCK₁-R)
  作者：Michela V. Pavan、Lucia Lassiani、Federico Berti、Giorgio Stefancich、Alessia Ciogli、Francesco Gasparrini、Laura Mennuni、Flora Ferrari、Chantal Escrieut、Esther Marco、Francesco Makovec、Daniel Fourmy、Antonio Varnavas

  DOI：10.1021/jm200438b

  日期：2011.8.25

  The anthranilic acid diamides represent the most recent class of nonpeptide CCK1 receptor (CCK1-R) antagonists. Herein we describe the second phase of the anthranilic acid C-terminal optimization using nonproteinogenic amino acids containing a phenyl ring in their side chain. The Homo-Phe derivative 2 (VL-0797) enhanced 12-fold the affinity for the rat CCK1-R affinity and 15-fold for the human CCK1-R relative to the reference compound 12 (VL-0395). The eutomer of 2 (6) exhibited a nanomolar range affinity toward the human CCK1-R and was at least 400-fold selective for the CCK1-R over the CCK2-R. Molecular docking in the modeled CCK1-R and its validation by site-directed mutagenesis experiments showed that the 6 binding site overlaps that occupied by the C-terminal bioactive region of the natural agonist CCK. Owing to their interesting properties, new compounds provided by this study represent a solid basis for further advances aimed at synthesis of clinically valuable CCK1-R antagonists.