8-甲氧基咪唑并[1,2-a]吡嗪 | 142744-37-4

• 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: 8-甲氧基咪唑并[1,2-a]吡嗪
• 英文名称: 8-methoxyimidazo<1,2-a>pyrazine
• 英文别名: 8-methoxy-imidazo[1,2-a]pyrazine；6-Brom-8-methoxy-imidazo<1,2-a>pyrazin；8-Methoxyimidazo[1,2-A]pyrazine
• CAS: 142744-37-4
• 化学式: C₇H₇N₃O
• mdl: MFCD09835037
• 分子量: 149.152
• InChiKey: PVQZROXLZRBGKP-UHFFFAOYSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  8-甲氧基咪唑并[1,2-a]吡嗪 在 硫酸 、 硝酸 作用下， 反应 3.0h， 以30%的产率得到8-Methoxy-3-nitro-imidazo[1,2-a]pyrazine
  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：

  6-溴-8-甲氧基咪唑并[1,2-A]吡嗪 在 palladium on activated charcoal 氢气 作用下， 生成 8-甲氧基咪唑并[1,2-a]吡嗪
  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

• PYRROLO[2,3-d]PYRIMIDINE TROPOMYSIN-RELATED KINASE INHIBITORS
  申请人：Andrews Mark David

  公开号：US20120258950A1

  公开（公告）日：2012-10-11

  The present invention relates to compounds of Formula (I) and their pharmaceutically acceptable salts, wherein the substituents are as described herein, and their use in medicine, in particular as Trk antagonists.

  本发明涉及式(I)化合物及其药学上可接受的盐，其中取代基如本文所述，并且它们在医学上的用途，特别是作为Trk拮抗剂。
• Novel imidazo based heterocycles
  申请人：Calderwood J. David

  公开号：US20070099925A1

  公开（公告）日：2007-05-03

  The present invention is directed to novel imidazopyrazine and imidazopyrimidine compounds of formula (I) wherein the variables are as defined herein. The compounds of formula (I) are useful as kinase inhibitors and as such would be useful in treating certain conditions and diseases, especially inflammatory conditions and diseases and proliferative disorders and conditions, for example, cancers.

  本发明涉及式（I）的新型咪唑吡嗪和咪唑嘧啶化合物，其中变量如在此定义。式（I）的化合物可用作激酶抑制剂，因此可用于治疗某些疾病和病症，特别是炎症性疾病和增殖性疾病和病症，例如癌症。
• US7709468B2
  申请人：——

  公开号：US7709468B2

  公开（公告）日：2010-05-04
• US8846698B2
  申请人：——

  公开号：US8846698B2

  公开（公告）日：2014-09-30
• Synthesis and antibronchospastic activity of 8-alkoxy- and 8-(alkylamino)imidazo[1,2-a]pyrazines
  作者：Pierre A. Bonnet、Alain Michel、Florence Laurent、Claire Sablayrolles、Eliane Rechencq、Jean C. Mani、Maurice Boucard、Jean P. Chapat

  DOI：10.1021/jm00096a008

  日期：1992.9

  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.