6-溴-N-乙基咪唑并[1,2-a]吡嗪-8-胺 | 117718-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡嗪类
• 中文名称: 6-溴-N-乙基咪唑并[1,2-a]吡嗪-8-胺
• 英文名称: 6-bromo-8-(ethylamino)imidazo<1,2-α>pyrazine
• 英文别名: Imidazo(1,2-a)pyrazin-8-amine, 6-bromo-N-ethyl-；6-bromo-N-ethylimidazo[1,2-a]pyrazin-8-amine
• CAS: 117718-86-2
• 化学式: C₈H₉BrN₄
• 分子量: 241.09
• InChiKey: STIRLFBTSNDDBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-溴-N-乙基咪唑并[1,2-a]吡嗪-8-胺 在 硫酸 、 硝酸 作用下， 反应 3.0h， 以55%的产率得到(6-Bromo-3-nitro-imidazo[1,2-a]pyrazin-8-yl)-ethyl-amine
  参考文献：
  名称：

  咪唑并[1,2- a ]吡嗪系列的硝化反应。实验和计算结果

  摘要：

  在一系列咪唑并[1,2- a ]吡嗪衍生物上进行硝化。分析了不同取代的衍生物和所有取代位置的反应性，并将实验结果与13 nmr数据和半经验计算（AMI）进行了比较。尽管未取代的杂环对硝化具有很高的抵抗力，但供电子基团，例如8位上的烷氧基或烷基氨基，可增强咪唑并[1,2- a ]吡嗪衍生物对亲电取代，特别是硝化的反应性。在13-nmr实验，电子分布和以中性形式计算的分子静电势等密度面与实验结果非常吻合，表明位置3是硝化反应中最活泼的位置。

  DOI：

  10.1002/jhet.5570340301
• 作为产物：
  描述：

  乙胺 、 6,8-二溴咪唑并[1,2-a]吡嗪 以 水 为溶剂， 反应 12.0h， 生成 6-溴-N-乙基咪唑并[1,2-a]吡嗪-8-胺
  参考文献：
  名称：

  Synthesis and antibronchospastic activity of 8-alkoxy- and 8-(alkylamino)imidazo[1,2-a]pyrazines

  摘要：

  Theophylline still occupies a dominant place in asthma therapy. Unfortunatly its adverse central nervous system (CNS) stimulant effects can dramatically limit its use, and adjustments in the dosage are often needed. We have synthesized a new series of imidazo[1,2-a]pyrazine derivatives which are much more potent bronchodilators than theophylline in vivo and do not exhibit the CNS stimulatory profile. In vitro studies on isolated rat uterus and guinea pig trachea confirm the high potentialities of these derivatives. 6-Bromo-8-(methylamino)imidazo[1,2-a]pyrazine-3-carbonitrile (23) is identified as the most potent compound of the series. As in the case of theophylline, phosphodiesterase inhibition appears unlikely to be the unique mechanism of action of this series of heterocycles.

  DOI：

  10.1021/jm00096a008

文献信息

• New imidazo[1,2-a]pyrazine derivatives with bronchodilatory and cyclic nucleotide phosphodiesterase inhibitory activities
  作者：Olivier Vitse、Florence Laurent、Tristan M. Pocock、Véronique Bénézech、Lahcen Zanik、Keith R.F. Elliott、Guy Subra、Karine Portet、Jacques Bompart、Jean-Pierre Chapat、Roger C. Small、Alain Michel、Pierre-Antoine Bonnet

  DOI：10.1016/s0968-0896(99)00019-x

  日期：1999.6

  lNew imidazo[1,2-a]pyrazine derivatives have been synthesized either by direct cyclization from pyrazines or by electrophilic substitutions: The presence nf electron donating groups On position 8 greatly enhances the reactivity of the heterocycle towards such reactions on position 3 of the heterocycle. The activities of these derivatives in trachealis muscle relaxation and in inhihiting cyclic nucleotide phosphodiesterase(PDE) isoenzyme types III and IV have been assessed All compounds demonstrated higher relaxant potency than theophylline. All the derivatives were moderately potent in inhibiting the type IV isoenzyme of PDE but only those with a cyano group on position 2 were potent in inhibiting the type III isoenzyme. (C) 1999 Elsevier Science Ltd. All rights reserved.
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