2(R,S)-[2-(2-adamantan-1-yl-acetylamino)-benzoylamino]-3-phenyl-propionic acid ethyl ester | 620167-45-5

• 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: 2(R,S)-[2-(2-adamantan-1-yl-acetylamino)-benzoylamino]-3-phenyl-propionic acid ethyl ester
• CAS: 620167-45-5
• 化学式: C₃₀H₃₆N₂O₄
• 分子量: 488.627
• InChiKey: QRISGRWFEJNBEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.5
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2(R,S)-[2-(2-adamantan-1-yl-acetylamino)-benzoylamino]-3-phenyl-propionic acid ethyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以40%的产率得到2-[2-(2-Adamantan-1-yl-acetylamino)-benzoylamino]-3-phenyl-propionic acid
  参考文献：
  名称：

  Anthranilic acid derivatives: a new class of non-peptide CCK1 receptor antagonists

  摘要：

  Having successfully obtained new CCK1 ligands holding appropriate groups on the anthranilic acid dimer used as molecular scaffold we were interested in increasing their micromolar affinity for the CCK1 receptors by modifying the spatial relationship of the main pharmacophoric groups. Since, we have proposed simplified analogues reducing the anthranilic acid dimer to a monomer. In this stage of our research program we have prepared and tested on CCK receptors a series of N-substituted anthranilic acid derivatives keeping a Phe residue at the C-terminal site. The indole-2-carbonyl group imparts the best CCK1 receptor binding affinity (compound 1: IC50 = 197.5 nM) while a sharp decrease in binding affinity is observed for the other indole containing derivatives. Moreover, in order to support the different binding behaviour observed for the synthesized compounds, a conformational investigation was carried out. Finally, on the basis of the main pharmacophoric groups of the obtained new lead compound (1) (coded VL-0395) a receptor binding hypothesis has been provided. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00475-3
• 作为产物：
  描述：

  靛红酸酐 在 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 2(R,S)-[2-(2-adamantan-1-yl-acetylamino)-benzoylamino]-3-phenyl-propionic acid ethyl ester
  参考文献：
  名称：

  Anthranilic acid derivatives: a new class of non-peptide CCK1 receptor antagonists

  摘要：

  Having successfully obtained new CCK1 ligands holding appropriate groups on the anthranilic acid dimer used as molecular scaffold we were interested in increasing their micromolar affinity for the CCK1 receptors by modifying the spatial relationship of the main pharmacophoric groups. Since, we have proposed simplified analogues reducing the anthranilic acid dimer to a monomer. In this stage of our research program we have prepared and tested on CCK receptors a series of N-substituted anthranilic acid derivatives keeping a Phe residue at the C-terminal site. The indole-2-carbonyl group imparts the best CCK1 receptor binding affinity (compound 1: IC50 = 197.5 nM) while a sharp decrease in binding affinity is observed for the other indole containing derivatives. Moreover, in order to support the different binding behaviour observed for the synthesized compounds, a conformational investigation was carried out. Finally, on the basis of the main pharmacophoric groups of the obtained new lead compound (1) (coded VL-0395) a receptor binding hypothesis has been provided. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00475-3