5-(ethoxycarbonyl)-3-methyl-1H-indole-2-carboxylic acid | 1312690-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-(ethoxycarbonyl)-3-methyl-1H-indole-2-carboxylic acid
• 英文别名: 5-ethoxycarbonyl-3-methyl-1H-indole-2-carboxylic acid
• CAS: 1312690-33-7
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: JQJXPLZQZQGFDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  471.8±40.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  79.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  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 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.75h， 生成 (S)-2-((2,6-diaminohexanamido)butylcarbamoyl)-3-methyl-1H-indole-5-carboxylic acid
  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：

  2-酮丁酸 、 4-氨基-3-碘苯甲酸乙酯 在 三乙烯二胺 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以65%的产率得到5-(ethoxycarbonyl)-3-methyl-1H-indole-2-carboxylic acid
  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

文献信息

• Synthesis and evaluation of bidentate ligands designed to interact with PDZ domains
  作者：Benjamin Boucherle、Alexandre Vogrig、Hemantkumar Deokar、Naoual Bouzidi、Isabelle Ripoche、Isabelle Thomas、Philippe Marin、Sylvie Ducki

  DOI：10.1016/j.bmc.2011.05.036

  日期：2011.7

  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.