2-((2-carboxyethyl)carbamoyl)-6-methyl-3-phenethyl-1H-indole-5-carboxylic acid | 1015464-79-5

• 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: 2-((2-carboxyethyl)carbamoyl)-6-methyl-3-phenethyl-1H-indole-5-carboxylic acid
• 英文别名: 2-(2-carboxyethylcarbamoyl)-6-methyl-3-(2-phenylethyl)-1H-indole-5-carboxylic acid
• CAS: 1015464-79-5
• 化学式: C₂₂H₂₂N₂O₅
• 分子量: 394.427
• InChiKey: KOZCWSDHKGGEBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-(3-(benzyloxy)-3-oxopropylcarbamoyl)-6-methyl-3-phenethyl-1H-indole-5-carboxylate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.0h， 生成 2-((2-carboxyethyl)carbamoyl)-6-methyl-3-phenethyl-1H-indole-5-carboxylic acid
  参考文献：
  名称：

  Rational design of the first small-molecule antagonists of NHERF1/EBP50 PDZ domains

  摘要：

  This report describes the first small-molecule antagonists that specifically target the ligand-binding pocket of PDZ domains of NHERF1 multi-functional adaptor protein. Comparison of the peptide sequence homology between the native ligand of NHERF1 PDZ domains and an indole-based non-peptide chemical scaffold allowed the design of a small-molecule antagonist of NHERF1 PDZ domains. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.038

文献信息

• Indole-2-amide based biochemical antagonist of Dishevelled PDZ domain interaction down-regulates Dishevelled-driven Tcf transcriptional activity
  作者：Neeraj Mahindroo、Chandanamali Punchihewa、Allison M. Bail、Naoaki Fujii

  DOI：10.1016/j.bmcl.2007.12.039

  日期：2008.2

  We designed and synthesized a series of indole-2-amide-based compounds that antagonize interaction between the Dishevelled (Dvl) PDZ domain and a peptide derived from the natural PDZ ligand Frizzled-7 (Fz7). These compounds inhibit Tcf-mediated transcription activated by exogenous Dvl via the biochemical antagonism. We confirmed tumor cell-selective activation of caspases by these compounds. (C) 2007 Elsevier Ltd. All rights reserved.
• Rational design of the first small-molecule antagonists of NHERF1/EBP50 PDZ domains
  作者：Anand Mayasundari、Antonio M. Ferreira、Liwen He、Neeraj Mahindroo、Don Bashford、Naoaki Fujii

  DOI：10.1016/j.bmcl.2007.12.038

  日期：2008.2

  This report describes the first small-molecule antagonists that specifically target the ligand-binding pocket of PDZ domains of NHERF1 multi-functional adaptor protein. Comparison of the peptide sequence homology between the native ligand of NHERF1 PDZ domains and an indole-based non-peptide chemical scaffold allowed the design of a small-molecule antagonist of NHERF1 PDZ domains. (C) 2007 Elsevier Ltd. All rights reserved.