4-benzylpiperazine-1-yl-(1H-indol-7-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-7-yl)methanone
• 英文别名: 1-[(1H-indol-7-yl)carbonyl]-4-(phenylmethyl)piperazine；(4-Benzyl-piperazin-1-yl)-(1H-indol-7-yl)-methanone；(4-benzylpiperazin-1-yl)-(1H-indol-7-yl)methanone
• 化学式: C₂₀H₂₁N₃O
• 分子量: 319.406
• InChiKey: PVAQDJVMUHSIQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  7-吲哚甲酸 、 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-7-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

• Indole-7-carboxamide derivatives as analgesics
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0599240A1

  公开（公告）日：1994-06-01

  This invention relates to indole-7-carboxamide derivatives of the formula where R₁ through R₆ are independently H, loweralkyl, and aralkyl; and in addition R₃ and R₅ can be joined together to form a piperazine ring of the formula where R₇ is H, loweralkyl, aryl, arylloweralkyl, pyrimidyl; and R₄ and R₅ can be joined together to form a pyrrolidine ring of the formula where R₈ is H, loweralkyl, arylloweralkyl; X is H, loweralkyl, halogen, NO₂, CF₃, NH₂, and OR₉; where R₉ is loweralkyl, arylloweralkyl and n is an integer of 1 to 3; and the pharmaceutically acceptable acid addition salts thereof and the optical isomers thereof where such isomers exist.

  本发明涉及式中的吲哚-7-甲酰胺衍生物 其中 R₁ 至 R₆ 独立地为 H、低级烷基和芳烷基；此外，R₃ 和 R₅ 可以连接在一起，形成式中的哌嗪环 其中 R₇ 是 H、低级烷基、芳基、芳低级烷基、嘧啶基；R₄ 和 R₅ 可以连接在一起，形成式中的吡咯烷环。 其中 R₈ 是 H、低级烷基、芳基低级烷基；X 是 H、低级烷基、卤素、NO₂、CF₃、NH₂ 和 OR₉；其中 R𠢙 是低级烷基、芳基低级烷基，n 是 1 至 3 的整数；以及它们的药学上可接受的酸加成盐和它们的光学异构体（如果存在此类异构体）。
• 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.
• US5330986A
  申请人：——

  公开号：US5330986A

  公开（公告）日：1994-07-19
• Indole-based heterocyclic inhibitors of p38α MAP kinase: designing a conformationally restricted analogue
  作者：Babu J Mavunkel、Sarvajit Chakravarty、John J Perumattam、Gregory R Luedtke、Xi Liang、Don Lim、Yong-jin Xu、Maureen Laney、David Y Liu、George F Schreiner、John A Lewicki、Sundeep Dugar

  DOI：10.1016/s0960-894x(03)00653-x

  日期：2003.9

  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.