ethyl 2-((6-((2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylpentanamido)hexyl)carbamoyl)-3-methyl-1H-indole-5-carboxylate | 1325676-33-2

• 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: ethyl 2-((6-((2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylpentanamido)hexyl)carbamoyl)-3-methyl-1H-indole-5-carboxylate
• CAS: 1325676-33-2
• 化学式: C₄₀H₄₈N₄O₆
• 分子量: 680.844
• InChiKey: KQCHLOLCEAHCKQ-LHAPQZOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  50.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  138.62
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-((6-((2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylpentanamido)hexyl)carbamoyl)-3-methyl-1H-indole-5-carboxylate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 24.0h， 以160 mg的产率得到sodium 2-(((2S,3S)-2-amino-3-methylpentanamido)-hexyl-carbamoyl)-3-methyl-1H-indole-5-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of bidentate ligands designed to interact with PDZ domains

  摘要：

  We designed bidentate ligands to target PDZ domains through two binding sites: site S0, delimited by the GLGF loop, and site S1, a zone situated around loop beta(B)/beta(C). A molecular docking study allowed us to design a generic S0 binder, to which was attached a variable size linker, itself linked to an amino acid aimed to interact with the S1 site of PDZ domains. A series of 15 novel bidentate ligands was prepared in 6-11 steps in good overall yield (24-43%). Some of these ligands showed an inhibitory activity against serotonin 5-HT2A receptor/PSD-95 interaction. This was assessed by pull-down assay using a synthetic decapeptide corresponding to the C-terminal residues of the receptor as a bait. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.036
• 作为产物：
  描述：

  5-(ethoxycarbonyl)-3-methyl-1H-indole-2-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.75h， 生成 ethyl 2-((6-((2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylpentanamido)hexyl)carbamoyl)-3-methyl-1H-indole-5-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of bidentate ligands designed to interact with PDZ domains

  摘要：

  We designed bidentate ligands to target PDZ domains through two binding sites: site S0, delimited by the GLGF loop, and site S1, a zone situated around loop beta(B)/beta(C). A molecular docking study allowed us to design a generic S0 binder, to which was attached a variable size linker, itself linked to an amino acid aimed to interact with the S1 site of PDZ domains. A series of 15 novel bidentate ligands was prepared in 6-11 steps in good overall yield (24-43%). Some of these ligands showed an inhibitory activity against serotonin 5-HT2A receptor/PSD-95 interaction. This was assessed by pull-down assay using a synthetic decapeptide corresponding to the C-terminal residues of the receptor as a bait. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.036