(2E)-3-(9-tert-butyl-6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepin-2-yl)-N-(4-methylphenyl)acrylamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-3-(9-tert-butyl-6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepin-2-yl)-N-(4-methylphenyl)acrylamide
• 英文别名: (E)-3-(9-tert-butyl-6-oxo-7,12-dihydro-5H-indolo[3,2-d][1]benzazepin-2-yl)-N-(4-methylphenyl)prop-2-enamide
• 化学式: C₃₀H₂₉N₃O₂
• 分子量: 463.579
• InChiKey: BPTCWBWRYKLYLR-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-tert-butyl-2-iodo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one 、 N-(4-甲基苯基)-2-丙烯酰胺 在 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以58%的产率得到(2E)-3-(9-tert-butyl-6-oxo-5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepin-2-yl)-N-(4-methylphenyl)acrylamide
  参考文献：
  名称：

  2-Arylpaullones are selective antitrypanosomal agents

  摘要：

  Antileishmanial paullone-chalcone hybrid molecules display antiparasitic activity against Trypanosoma brucei rhodesiense blood stream forms, albeit with low selectivity against human THP-1 cells. In order to develop less toxic analogues, paullones with acrylamide or aryl substituents in 2-position were synthesized, of which the latter exhibited potent antiparasitic activity with excellent selectivity profiles. The most potent compound identified in this study was 9-tert-butyl-2-(4-morpholinophenyl)paullone (3i) which inhibited the parasites at submicromolar concentrations (GI(50) = 510 nM) with a selectivity index of 157. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.065

文献信息

• 2-Arylpaullones are selective antitrypanosomal agents
  作者：Jasmin Ryczak、Ma'ayan Papini、Annette Lader、Abedelmajeed Nasereddin、Dmitry Kopelyanskiy、Lutz Preu、Charles L. Jaffe、Conrad Kunick

  DOI：10.1016/j.ejmech.2013.03.065

  日期：2013.6

  Antileishmanial paullone-chalcone hybrid molecules display antiparasitic activity against Trypanosoma brucei rhodesiense blood stream forms, albeit with low selectivity against human THP-1 cells. In order to develop less toxic analogues, paullones with acrylamide or aryl substituents in 2-position were synthesized, of which the latter exhibited potent antiparasitic activity with excellent selectivity profiles. The most potent compound identified in this study was 9-tert-butyl-2-(4-morpholinophenyl)paullone (3i) which inhibited the parasites at submicromolar concentrations (GI(50) = 510 nM) with a selectivity index of 157. (C) 2013 Elsevier Masson SAS. All rights reserved.