2-phenylimidazo[1,2-a]pyrazin-3-(7H)-one hydrochloride

• 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-phenylimidazo[1,2-a]pyrazin-3-(7H)-one hydrochloride
• 英文别名: 2-phenyl-7H-imidazo[1,2-a]pyrazin-3-one;hydrochloride
• 化学式: C₁₂H₉N₃O*ClH
• 分子量: 247.684
• InChiKey: AIVHUGMBXNJEJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.68
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  氨基吡嗪 、 苯基丙醇水合物 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 2-phenylimidazo[1,2-a]pyrazin-3-(7H)-one hydrochloride
  参考文献：
  名称：

  咪唑并吡嗪酮抗氧化剂对缺血/再灌注损伤的保护作用。

  摘要：

  合成了一系列2-取代的3,7-二氢咪唑并[1,2-a]吡嗪-3-酮，并对其抗氧化活性进行了评估。化合物1-8是AAPH诱导的脂质过氧化的抑制剂（体外），是抗缺血/再灌注中微血管损伤的出色保护剂（体内）。因此，腔肠素（荧光素）的典型双环结构可被视为药物化学中的有用先导。

  DOI：

  10.1016/s0960-894x(02)01049-1

文献信息

• Imidazolopyrazinones as potential antioxidants
  作者：Ingrid Devillers、Georges Dive、Catherine De Tollenaere、Bénédicte Falmagne、Bertrand de Wergifosse、Jean-François Rees、Jacqueline Marchand-Brynaert

  DOI：10.1016/s0960-894x(01)00445-0

  日期：2001.9

  A series of imidazolopyrazinones 3, substituted at C-2, and C-2/C-6, has been prepared. The compounds behaved as quenchers of superoxide anion. The more active compounds are structurally related to coelenterazine, a natural substrate of marine bioluminescence. Theoretical parameters based on Hartree-Fock instabilities hake been examined. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Chemistry around imidazopyrazine and ibuprofen: Discovery of novel fatty acid amide hydrolase (FAAH) inhibitors
  作者：Frédéric De Wael、Giulio G. Muccioli、Didier M. Lambert、Thérèse Sergent、Yves-Jacques Schneider、Jean-François Rees、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.ejmech.2010.04.040

  日期：2010.9

  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.