4-benzylpiperazine-1-yl-(1H-indol-4-yl)methanone

• 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: 4-benzylpiperazine-1-yl-(1H-indol-4-yl)methanone
• 英文别名: (4-benzylpiperazin-1-yl)(1H-indol-4-yl)methanone；(4-benzylpiperazin-1-yl)-(1H-indol-4-yl)methanone
• 化学式: C₂₀H₂₁N₃O
• 分子量: 319.406
• InChiKey: QGOAMMIGXAHGDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚-4-羧酸 、 1-苄基哌嗪 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-benzylpiperazine-1-yl-(1H-indol-4-yl)methanone
  参考文献：
  名称：

  Indole-based heterocyclic inhibitors of p38α MAP kinase: designing a conformationally restricted analogue

  摘要：

  p38alpha, Mitogen Activated Protein Kinase (MAP kinase) is an intracellular soluble serine threonine kinase. p38alpha kinase is activated in response to cellular stresses, growth factors and cytokines such as interleukin-1 (IL- 1) and tumor necrosis factor alpha (TNF-alpha). The central role of p38alpha activation in settings of both chronic and acute inflammation has led efforts to find inhibitors of this enzyme as possible therapies for diseases such as rheumatoid arthritis, where p38alpha activation is thought to play a causal role. Herein, we report structure-activity relationship studies on a series of indole-based heterocyclic inhibitors that led to the design and identification of a new class of p38alpha inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00653-x

文献信息

• Palladium-Catalyzed Carbonylation of Haloindoles:  No Need for Protecting Groups
  作者：Kamal Kumar、Alexander Zapf、Dirk Michalik、Annegret Tillack、Timo Heinrich、Henning Böttcher、Michael Arlt、Matthias Beller

  DOI：10.1021/ol035988r

  日期：2004.1.1

  For the first time, palladium-catalyzed carbonylations of unprotected bromoindoles have been performed successfully with different N- and O-nucleophiles. Various indole carboxylic acid derivatives are accessible in excellent yield. For example, aminocarbonylation of 4-, 5-, 6-, or 7-bromoindole with arylethylpiperazines provides a direct one-step synthesis for CNS active amphetamine derivatives.