5-bromo-1-propyl-1H-pyrrolo[2,3-b]pyridine | 1440956-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 5-bromo-1-propyl-1H-pyrrolo[2,3-b]pyridine
• 英文别名: 5-Bromo-1-propylpyrrolo[2,3-b]pyridine
• CAS: 1440956-68-2
• 化学式: C₁₀H₁₁BrN₂
• 分子量: 239.115
• InChiKey: BKQTXFPDRRRXJC-UHFFFAOYSA-N

物化性质

• 沸点：
  318.9±22.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromo-1-propyl-1H-pyrrolo[2,3-b]pyridine 在 叔丁基锂 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 N-propyl-7-azaindole
  参考文献：
  名称：

  A Closer Look at the Bromine–Lithium Exchange with tert-Butyllithium in an Aryl Sulfonamide Synthesis

  摘要：

  A practical protocol for the one-pot synthesis of various aryl sulfonamides, notably of pyridine-core-substituted 7-azaindolyl sulfonamides, Is described. A key step is the well-known bromine-lithium exchange reaction of an aryl bromide with tert-butyllithium (t-BuLi). Differing from the common practice to use 2 or more equiv of organolithium, the exact amount of t-BuLi needed for a sufficient exchange reaction Is determined for each aryl bromide in a GC-MS-assisted experiment.

  DOI：

  10.1021/ol4010454
• 作为产物：
  描述：

  溴丙烷 、 5-溴-7-氮杂吲哚 在 sodium hydride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.5h， 以97%的产率得到5-bromo-1-propyl-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  A Closer Look at the Bromine–Lithium Exchange with tert-Butyllithium in an Aryl Sulfonamide Synthesis

  摘要：

  A practical protocol for the one-pot synthesis of various aryl sulfonamides, notably of pyridine-core-substituted 7-azaindolyl sulfonamides, Is described. A key step is the well-known bromine-lithium exchange reaction of an aryl bromide with tert-butyllithium (t-BuLi). Differing from the common practice to use 2 or more equiv of organolithium, the exact amount of t-BuLi needed for a sufficient exchange reaction Is determined for each aryl bromide in a GC-MS-assisted experiment.

  DOI：

  10.1021/ol4010454

文献信息

• Novel fluorine-18 labeled 5-(1-pyrrolidinylsulfonyl)-7-azaisatin derivatives as potential PET tracers for in vivo imaging of activated caspases in apoptosis
  作者：Christopher M. Waldmann、Sven Hermann、Andreas Faust、Burkhard Riemann、Otmar Schober、Michael Schäfers、Günter Haufe、Klaus Kopka

  DOI：10.1016/j.bmc.2015.07.014

  日期：2015.9

  The programmed type I cell death, defined as apoptosis, is induced by complex regulated signaling pathways that trigger the intracellular activation of executioner caspases-3, -6 and -7. Once activated, these enzymes initiate cellular death through cleavage of proteins which are responsible for DNA repair, signaling and cell maintenance. Several radiofluorinated inhibitors of caspases-3 and -7, comprising a moderate lipophilic 5-(1-pyrrolidinylsulfonyl)isatin lead structure, are currently being investigated for imaging apoptosis in vivo by us and others. The purpose of this study was to increase the intrinsic hydrophilicity of the aforementioned lead structure to alter the pharmacokinetic behavior of the resulting caspase-3 and -7 targeted radiotracer. Therefore, fluorinated and non-fluorinated derivatives of 5-(1-pyrrolidinylsulfonyl)-7-azaisatin were synthesized and tested for their inhibitory properties against recombinant caspases-3 and -7. Fluorine-18 has been introduced by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) of an alkyne precursor with 2-[F-18]fluoroethylazide. Using dynamic micro-PET biodistribution studies in vivo the kinetic behavior of one promising PET-compatible 5-pyrrolidinylsulfonyl 7-azaisatin derivative has been compared to a previously described isatin based radiotracer. (C) 2015 Elsevier Ltd. All rights reserved.