2-phenyl-6-p-hydroxyphenylimidazo[1,2-a]pyrazin-3(7H)-imine hydrochloride | 1246302-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-6-p-hydroxyphenylimidazo[1,2-a]pyrazin-3(7H)-imine hydrochloride
• CAS: 1246302-64-6
• 化学式: C₁₈H₁₄N₄O*ClH
• 分子量: 338.796
• InChiKey: FHMRARMMFRKJQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.69
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-异亚硝基苯乙酮 、 5-(4-hydroxyphenyl)-2-aminopyrazine 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.08h， 以30%的产率得到2-phenyl-6-p-hydroxyphenylimidazo[1,2-a]pyrazin-3(7H)-imine hydrochloride
  参考文献：
  名称：

  Chemistry around imidazopyrazine and ibuprofen: Discovery of novel fatty acid amide hydrolase (FAAH) inhibitors

  摘要：

  Based on the imidazo-[1,2-a]-pyrazin-3-(7H)-one scaffold, a dual action prodrug has been designed for combining antioxidant and anti-inflammatory activities, possibly unmasked upon oxidation. The construction of the target-molecule requires two building blocks, namely a 2-amino-1,4-pyrazine and a 2-ketoaldehyde. Attempts to synthesize the 2-ketoaldehyde (5a) derived from ibuprofen failed, but led to the corresponding 2-ketoaldoxime (7a) which could not be condensed with the pyrazine synthons. However, a model compound, i.e. phenylglyoxal aldoxime, reacted well under microwave activation to furnish novel imidazo[1,2-a]-pyrazine-3-(7H)-imine derivatives (18a,b). These heterobicycles behave as antioxidants by inhibiting the lipid peroxidation, and one compound (18b) is endowed with a significant anti-inflammatory effect in a cellular test. Unexpectedly, all the synthetic intermediates derived from ibuprofen are good inhibitors of FAAH, the most active compound (4a) featuring the 1,3-dithian-2-yl motif. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.040