N-(4-imino-8-(4-methoxyphenylamino)pyrimido[5,4-d]pyrimidin-3(4H)-yl) isonicotinamide | 1234199-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(4-imino-8-(4-methoxyphenylamino)pyrimido[5,4-d]pyrimidin-3(4H)-yl) isonicotinamide
• 英文别名: N-[4-imino-8-(4-methoxyanilino)pyrimido[5,4-d]pyrimidin-3-yl]pyridine-4-carboxamide
• CAS: 1234199-94-0
• 化学式: C₁₉H₁₆N₈O₂
• 分子量: 388.388
• InChiKey: VSPFVVUFEKAARX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 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：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  异烟肼 、 6-cyano-9-(4-methoxyphenyl)-9H-purine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 为溶剂， 以79%的产率得到N-(4-imino-8-(4-methoxyphenylamino)pyrimido[5,4-d]pyrimidin-3(4H)-yl) isonicotinamide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of substituted pyrimido[5,4-d]pyrimidines as a novel class of Antimycobacterium tuberculosis agents

  摘要：

  Novel pyrimido[5,4-d]pyrimidines were efficiently synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis strain H(37)Rv. This new structural class of compounds showed high activity against the bacilli. The activity depends on the substituents present in N-3 and C-8 of the pyrimido[5,4-d]pyrimidine core. Compounds having a 4-MeOC(6)H(4), a Ph or a 4-FC(6)H(4) group as the substituent on C-8 and a 4'-pyridinyl, a Ph or 2'-furyl group as the substituent on N-3 were active. The highest activity was registered for compounds having 4-FC(6)H(4) or 4-MeOC(6)H(4) as substituents in C-8 and a heteroaryl group as substituent in N-3. The new compounds showed high potency and promising antitubercular activity, as is the case of N[8-[(4-fluorophenyl)amino]-4-iminopyrimido[5,4-d]pyrimidin-3(4H)-yl]isonicotinamide with an IC(90) = 3.58 mu g/mL, and should be regarded as new hits for further development as a novel class of Antimycobacterium tuberculosis agents. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.047

文献信息

• Synthesis and in vitro evaluation of substituted pyrimido[5,4-d]pyrimidines as a novel class of Antimycobacterium tuberculosis agents
  作者：Ana H. Bacelar、M. Alice Carvalho、M. Fernanda Proença

  DOI：10.1016/j.ejmech.2010.03.047

  日期：2010.7

  Novel pyrimido[5,4-d]pyrimidines were efficiently synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis strain H(37)Rv. This new structural class of compounds showed high activity against the bacilli. The activity depends on the substituents present in N-3 and C-8 of the pyrimido[5,4-d]pyrimidine core. Compounds having a 4-MeOC(6)H(4), a Ph or a 4-FC(6)H(4) group as the substituent on C-8 and a 4'-pyridinyl, a Ph or 2'-furyl group as the substituent on N-3 were active. The highest activity was registered for compounds having 4-FC(6)H(4) or 4-MeOC(6)H(4) as substituents in C-8 and a heteroaryl group as substituent in N-3. The new compounds showed high potency and promising antitubercular activity, as is the case of N[8-[(4-fluorophenyl)amino]-4-iminopyrimido[5,4-d]pyrimidin-3(4H)-yl]isonicotinamide with an IC(90) = 3.58 mu g/mL, and should be regarded as new hits for further development as a novel class of Antimycobacterium tuberculosis agents. (C) 2010 Elsevier Masson SAS. All rights reserved.