2-(4-(8-amino-3-oxo-2-phenyl-2,3-dihydro-1,2,4-triazolo-[4,3-a]pyrazin-6-yl)phenoxy)acetamide

• 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-(4-(8-amino-3-oxo-2-phenyl-2,3-dihydro-1,2,4-triazolo-[4,3-a]pyrazin-6-yl)phenoxy)acetamide
• 英文别名: 2-[4-(8-Amino-3-oxo-2-phenyl-[1,2,4]triazolo[4,3-a]pyrazin-6-yl)phenoxy]acetamide；2-[4-(8-amino-3-oxo-2-phenyl-[1,2,4]triazolo[4,3-a]pyrazin-6-yl)phenoxy]acetamide
• 化学式: C₁₉H₁₆N₆O₃
• 分子量: 376.374
• InChiKey: BWSCSSSMXYJTQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  8-amino-6-(4-hydroxyphenyl)-2-phenyl-[1,2,4]triazolo[4,3-a]pyrazin-3(2H)-one 、 氯乙酰胺 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以51%的产率得到2-(4-(8-amino-3-oxo-2-phenyl-2,3-dihydro-1,2,4-triazolo-[4,3-a]pyrazin-6-yl)phenoxy)acetamide
  参考文献：
  名称：

  Antioxidant-Conjugated 1,2,4-Triazolo[4,3-a]pyrazin-3-one Derivatives: Highly Potent and Selective Human A_2A Adenosine Receptor Antagonists Possessing Protective Efficacy in Neuropathic Pain

  摘要：

  New 8-amino-6-aryl-1,2,4-triazolo[4,3-a]pyrazin-3-ones were designed to obtain dual antioxidant-human A(2A) adenosine receptor (hA(2A) AR) antagonists. Two sets of compounds were synthesized, the first featuring phenol rings at the 6-position, the second bearing the lipoyl and 4-hydroxy-3,5-di-tertbut-benzoyl residues appended by different linkers on the 6-phenyl ring. Several new triazolopyrazines (1-21) were potent and selective hA(2A) AR antagonists (K-i = 0.17-54.5 nM). Compounds 11, 15, and 21, featuring antioxidant moieties, and compound 12, lacking the antioxidant functionality, reduced oxaliplatin-induced toxicity in microglia cells, the most active being the lipoyl-derivative 15 and the (4-hydroxy-3,5-di-tertbutyl)benzoyl-analogue 21 which were effective in reducing the oxygen free radical level. The lipoyl-derivative 15 was also able to revert oxaliplatin-induced neuropathy in the mouse. In vivo efficacy of 15 makes it a promising neuroprotective agent in oxidative stress-related diseases.

  DOI：

  10.1021/acs.jmedchem.9b00778