N-(4-bromobenzyl)-2-(1H-indol-3-yl)-2-oxoacetamide

• 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: N-(4-bromobenzyl)-2-(1H-indol-3-yl)-2-oxoacetamide
• 英文别名: N-[(4-bromophenyl)methyl]-2-(1H-indol-3-yl)-2-oxoacetamide
• 化学式: C₁₇H₁₃BrN₂O₂
• mdl: MFCD03715011
• 分子量: 357.206
• InChiKey: KSKJDFBKCIYONL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚-3-乙醛酰氯 、 对溴苄胺 在 三乙胺 作用下， 以 甲苯 为溶剂， 以92%的产率得到N-(4-bromobenzyl)-2-(1H-indol-3-yl)-2-oxoacetamide
  参考文献：
  名称：

  Novel N-Substituted Indol-3-ylglyoxylamides Probing the L_Di and L₁/L₂ Lipophilic Regions of the Benzodiazepine Receptor Site in Search for Subtype-Selective Ligands

  摘要：

  Novel N-substituted indol-3-ylglyoxylamides (10-37) were synthesized and evaluated as ligands of the benzodiazepine receptor (BzR). In an effort to achieve affinity-based selectivity among BzR subtypes, these compounds were designed to probe the L-Di and L-2 lipophilic regions. Taking the alpha(1)-selective benzylindolylglyoxylamides Ia and Ib as leads, we varied the substituent on the benzylamide phenyl ring (compounds 10-23) or replaced the benzyl moiety with alkyl groups (compounds 24-37). The above structural changes gave no shift of selectivity from the alpha(1) toward the alpha(2) or alpha(5) subtypes, thus confirming that a ligand which occupies the L-Di region probably exhibits alpha(1) selectivity, despite its interactions with other lipophilic areas in the receptor binding cleft. Compound 11 (N-(p-methylbenzyl)-5-nitroindol-3-ylglyoxylamide), which selectively binds with a full agonist efficacy at the alpha(1) receptor subtype and displays sedative action, can be regarded as an interesting potential zolpidem-like sedative-hypnotic agent.

  DOI：

  10.1021/jm0607707