N-benzyl-2-(1-benzyl-1H-indol-3-yl)-2-oxoacetamide | 55654-78-9

• 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-benzyl-2-(1-benzyl-1H-indol-3-yl)-2-oxoacetamide
• 英文别名: N-benzyl-2-(1-benzyl-indol-3-yl)-2-oxo-acetamide；N-benzyl-2-(1-benzylindol-3-yl)-2-oxoacetamide
• CAS: 55654-78-9
• 化学式: C₂₄H₂₀N₂O₂
• 分子量: 368.435
• InChiKey: SOBBQNAAVLCKDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚-3-乙醛酰氯 在 sodium hydride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 25.0h， 生成 N-benzyl-2-(1-benzyl-1H-indol-3-yl)-2-oxoacetamide
  参考文献：
  名称：

  Modulation of A2B adenosine receptor by 1-Benzyl-3-ketoindole derivatives

  摘要：

  We have disclosed a series of 1-benzyl-3-ketoindole derivatives acting as either positive or negative modulators of the human A2B adenosine receptor (A(2B) AR) depending on small differences in their side chain. The new compounds were designed taking into account structural similarities between AR antagonists and ligands of the GABAA/benzodiazepine receptor. All compounds resulted totally inactive at A(2A) and A(3) ARs and showed small (8a,b) or none (7a,b, 8c and 9a,b) affinity for A(1) AR. When tested on A(2B) AR-transfected CHO cells, 7a,b and 8a acted as positive modulators, whereas 8b,c and 9a,b acted as negative modulators, enhancing or weakening the NECA-induced increase of cAMP levels, respectively. Compounds 7-9 might be regarded as useful biological and pharmacological tools to explore the therapeutic potential of A(2B) AR modulators, while their 3-ketoindole scaffold might be taken as a reference to design new analogs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.001

文献信息

• Modulation of A2B adenosine receptor by 1-Benzyl-3-ketoindole derivatives
  作者：Sabrina Taliani、Maria Letizia Trincavelli、Barbara Cosimelli、Sonia Laneri、Elda Severi、Elisabetta Barresi、Isabella Pugliesi、Simona Daniele、Chiara Giacomelli、Giovanni Greco、Ettore Novellino、Claudia Martini、Federico Da Settimo

  DOI：10.1016/j.ejmech.2013.09.001

  日期：2013.11

  We have disclosed a series of 1-benzyl-3-ketoindole derivatives acting as either positive or negative modulators of the human A2B adenosine receptor (A(2B) AR) depending on small differences in their side chain. The new compounds were designed taking into account structural similarities between AR antagonists and ligands of the GABAA/benzodiazepine receptor. All compounds resulted totally inactive at A(2A) and A(3) ARs and showed small (8a,b) or none (7a,b, 8c and 9a,b) affinity for A(1) AR. When tested on A(2B) AR-transfected CHO cells, 7a,b and 8a acted as positive modulators, whereas 8b,c and 9a,b acted as negative modulators, enhancing or weakening the NECA-induced increase of cAMP levels, respectively. Compounds 7-9 might be regarded as useful biological and pharmacological tools to explore the therapeutic potential of A(2B) AR modulators, while their 3-ketoindole scaffold might be taken as a reference to design new analogs. (C) 2013 Elsevier Masson SAS. All rights reserved.