3-(4-methoxybenzylamino)pyrazine-2,5-dicarbonitrile | 1418269-61-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxybenzylamino)pyrazine-2,5-dicarbonitrile
• 英文别名: 3-[(4-Methoxyphenyl)methylamino]pyrazine-2,5-dicarbonitrile；3-[(4-methoxyphenyl)methylamino]pyrazine-2,5-dicarbonitrile
• CAS: 1418269-61-0
• 化学式: C₁₄H₁₁N₅O
• 分子量: 265.274
• InChiKey: QWUHTTCWLVCVKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  吡嗪酰胺 在 ammonium peroxydisulfate 、 双氧水 、 potassium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 3-(4-methoxybenzylamino)pyrazine-2,5-dicarbonitrile
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of pyrazinamide derivatives with benzylamino substitution

  摘要：

  A series of 19 new compounds related to pyrazinamide were synthesized, characterized with analytical data and screened for in vitro whole cell antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and two types of Mycobacterium avium. The series consisted of 3( benzylamino)-5-cyanopyrazine-2-carboxamides and 3-(benzylamino)pyrazine-2,5-dicarbonitriles with various substituents on the phenyl ring. RP-HPLC method was used to determine the lipophilicity of the prepared compounds. Nine compounds exerted similar or better activity against Mycobacterium tuberculosis compared to pyrazinamide (MIC = 6.25-12.5 mu g/mL). 3-(Benzylamino)pyrazine-2,5-dicarbonitrile inhibited all of the tested mycobacterial strains with MIC within the range 12.5-25 mu g/mL. Although not the most active, 4-NH2 substituted compounds possessed the lowest in vitro cytotoxicity (hepatotoxicity), leading to selectivity index SI = 5.5 and SI > 21. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.052