N-benzyl-N-ethyl-2-[2-(2-naphthyl)-1H-indol-3-yl]-2-oxoacetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-benzyl-N-ethyl-2-[2-(2-naphthyl)-1H-indol-3-yl]-2-oxoacetamide
• 英文别名: N-benzyl-N-ethyl-2-(2-naphthalen-2-yl-1H-indol-3-yl)-2-oxoacetamide
• 化学式: C₂₉H₂₄N₂O₂
• 分子量: 432.522
• InChiKey: VMQJAXRKVKZTFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-萘基)吲哚 在 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 N-benzyl-N-ethyl-2-[2-(2-naphthyl)-1H-indol-3-yl]-2-oxoacetamide
  参考文献：
  名称：

  Deepening the Topology of the Translocator Protein Binding Site by Novel N,N-Dialkyl-2-arylindol-3-ylglyoxylamides

  摘要：

  As a continuation of our studies on 2-phenylindol-3-ylglyoxylamides as potent and selective translocator protein (TSPO) ligands, two subsets of novel derivatives, featuring hydrophilic group (OH, NH2, COOH) at the para-position of the pendent 2-phenyl ring (8-16) or different 2-aryl moieties, namely, 3-thienyl, p-biphenyl, 2-naphthyl (23-35), were synthesized and biologically evaluated, some of them showing K-i values in the subnanomolar range and the 2-naphthyl group performance being the best. The resulting SARs confirmed the key role played by interactions taking place between ligands and the lipophilic Li pocket of the TSPO binding site. Docking simulations were performed on the most potent compound of the present series (29) exploiting the recently available 3D structures of TSPO bound to its standard ligand (PK11195). Our theoretical model was fully consistent with SARs of the newly investigated as well of the previously reported 2-phenylindol-3-ylglyoxylamide derivatives.

  DOI：

  10.1021/acs.jmedchem.5b00689

文献信息

• Deepening the Topology of the Translocator Protein Binding Site by Novel <i>N</i>,<i>N</i>-Dialkyl-2-arylindol-3-ylglyoxylamides
  作者：Elisabetta Barresi、Agostino Bruno、Sabrina Taliani、Sandro Cosconati、Eleonora Da Pozzo、Silvia Salerno、Francesca Simorini、Simona Daniele、Chiara Giacomelli、Anna Maria Marini、Concettina La Motta、Luciana Marinelli、Barbara Cosimelli、Ettore Novellino、Giovanni Greco、Federico Da Settimo、Claudia Martini

  DOI：10.1021/acs.jmedchem.5b00689

  日期：2015.8.13

  As a continuation of our studies on 2-phenylindol-3-ylglyoxylamides as potent and selective translocator protein (TSPO) ligands, two subsets of novel derivatives, featuring hydrophilic group (OH, NH2, COOH) at the para-position of the pendent 2-phenyl ring (8-16) or different 2-aryl moieties, namely, 3-thienyl, p-biphenyl, 2-naphthyl (23-35), were synthesized and biologically evaluated, some of them showing K-i values in the subnanomolar range and the 2-naphthyl group performance being the best. The resulting SARs confirmed the key role played by interactions taking place between ligands and the lipophilic Li pocket of the TSPO binding site. Docking simulations were performed on the most potent compound of the present series (29) exploiting the recently available 3D structures of TSPO bound to its standard ligand (PK11195). Our theoretical model was fully consistent with SARs of the newly investigated as well of the previously reported 2-phenylindol-3-ylglyoxylamide derivatives.