6-(2,4-dinitrophenyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione | 1403980-64-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(2,4-dinitrophenyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione
• 英文别名: 6-(2,4-Dinitrophenyl)pyrrolo[3,4-b]pyrazine-5,7-dione；6-(2,4-dinitrophenyl)pyrrolo[3,4-b]pyrazine-5,7-dione
• CAS: 1403980-64-2
• 化学式: C₁₂H₅N₅O₆
• 分子量: 315.202
• InChiKey: QDGILLWDPXFBGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  155
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,3-吡嗪二酸酐 、 2,4-二硝基苯胺 在 sodium acetate 、 溶剂黄146 、 碳酸氢钠 作用下， 以87%的产率得到6-(2,4-dinitrophenyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione
  参考文献：
  名称：

  Synthesis, molecular modeling study, preliminary antibacterial, and antitumor evaluation of N-substituted naphthalimides and their structural analogues

  摘要：

  Carboxylic acid imides 1-26 have been synthesized and screened for their antibacterial against gram-positive and gram-negative organisms and their antitumor activity against 60 tumor cell lines taken from nine different organs. Compounds 12, 14, and 16 were the most active and broad-spectrum antibacterial member in this study. Compound 9 showed the most cytotoxicity with a significant inhibition for renal cancer cells. 2D-QSAR study provides details on the fine relationship linking structure and activity and offers clues for structural modifications that can improve the activity. Docking study of the compounds 12, 14, and 16 into the active site of the topoisomerase II DNA gyrase enzymes revealed a similar binding mode to bound inhibitor Clorobiocin.

  DOI：

  10.1007/s00044-012-0230-8

文献信息

• Synthesis, molecular modeling study, preliminary antibacterial, and antitumor evaluation of N-substituted naphthalimides and their structural analogues
  作者：Adel S. El-Azab、Amer M. Alanazi、Naglaa I. Abdel-Aziz、Ibrahim A. Al-Suwaidan、Magda A. A. El-Sayed、Magda A. El-Sherbeny、Alaa A.-M. Abdel-Aziz

  DOI：10.1007/s00044-012-0230-8

  日期：2013.5

  Carboxylic acid imides 1-26 have been synthesized and screened for their antibacterial against gram-positive and gram-negative organisms and their antitumor activity against 60 tumor cell lines taken from nine different organs. Compounds 12, 14, and 16 were the most active and broad-spectrum antibacterial member in this study. Compound 9 showed the most cytotoxicity with a significant inhibition for renal cancer cells. 2D-QSAR study provides details on the fine relationship linking structure and activity and offers clues for structural modifications that can improve the activity. Docking study of the compounds 12, 14, and 16 into the active site of the topoisomerase II DNA gyrase enzymes revealed a similar binding mode to bound inhibitor Clorobiocin.