N-benzyl-3-formyl-1H-indole-1-carboxamide | 1195785-12-6

• 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-3-formyl-1H-indole-1-carboxamide
• CAS: 1195785-12-6
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: NNWORSQITIBCDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.1
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-formyl-1H-indole-1-carboxamide 、 3-氨基-5-苯基吡唑 在 aluminum (III) chloride 作用下， 以 甲醇 为溶剂， 生成 1-benzyl-3-[2-(3-phenyl-2H-pyrazolo[3,4-b]pyridin-5-yl)phenyl]urea
  参考文献：
  名称：

  An Efficient One-Step Synthesis of Heterobiaryl Pyrazolo[3,4-b]pyridines via Indole Ring Opening

  摘要：

  A mild one-step synthetic method to access privileged heterobiaryl pyrazolo[3,4-b]pyridines from indole-3-carboxaldehyde derivatives and a variety of aminopyrazoles has been developed. This novel method constructs heterobiaryls with the wide scope of substrate generality and excellent regioselectivity via indole ring opening.

  DOI：

  10.1021/ol902147u
• 作为产物：
  描述：

  3-吲哚甲醛 、 异氰酸苄酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以78%的产率得到N-benzyl-3-formyl-1H-indole-1-carboxamide
  参考文献：
  名称：

  An Efficient One-Step Synthesis of Heterobiaryl Pyrazolo[3,4-b]pyridines via Indole Ring Opening

  摘要：

  A mild one-step synthetic method to access privileged heterobiaryl pyrazolo[3,4-b]pyridines from indole-3-carboxaldehyde derivatives and a variety of aminopyrazoles has been developed. This novel method constructs heterobiaryls with the wide scope of substrate generality and excellent regioselectivity via indole ring opening.

  DOI：

  10.1021/ol902147u

文献信息

• Ruthenium/Iridium-Catalyzed C-2 Activation of Indoles with Bicyclic Olefins: An Easy Access to Functionalized Heterocyclic Motifs
  作者：K. Radhakrishnan、P. Aparna、Ajesh Vijayan、Saran Raveendran、E. Suresh、R. Varma

  DOI：10.1055/s-0036-1588676

  日期：——

  Selective C-2 functionalization of N-protected and free indoles is reported. The ruthenium-catalyzed C-2 activation of indoles provided an easy access to cyclopentenylated indoles. Hydroheteroarylated bicyclic motifs were synthesized via iridium-catalyzed C-2 activation of NH indoles. The methodology was extended to different bicyclic adducts such as diaza- or urea-derived bicyclic olefins.

  报道了 N 保护和游离吲哚的选择性 C-2 功能化。钌催化的吲哚的 C-2 活化为获得环戊烯化吲哚提供了便利。氢杂芳基化双环基序是通过铱催化的 NH 吲哚的 C-2 活化合成的。该方法被扩展到不同的双环加合物，例如二氮杂或脲衍生的双环烯烃。
• Discovery of a highly selective FLT3 kinase inhibitor from phenotypic cell viability profiling
  作者：Sanghee Lee、Ala Jo、Seung Bum Park

  DOI：10.1039/c2md20169k

  日期：——

  We discovered a novel heterobiaryl pyrazolopyridine skeleton as a selective FLT3 inhibitor from phenotype-based viability profiling and hypothesis-driven deconvolution.

  我们从基于表型的存活率分析和假设驱动的解析中发现了一种新颖的异双芳基吡唑吡啶骨架作为选择性FLT3抑制剂。