6-Azido-7-chloroquinoxaline-5,8-dione | 218271-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Azido-7-chloroquinoxaline-5,8-dione
• CAS: 218271-01-3
• 化学式: C₈H₂ClN₅O₂
• 分子量: 235.589
• InChiKey: UDZDLBUZILGPRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Azido-7-chloroquinoxaline-5,8-dione 在 sodium tetrahydroborate 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 N-(7-chloro-5,8-dioxoquinoxalin-6-yl)acetamide
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 2-Methyl-4,9-dihydro-1-substituted-1H-imidazo[4,5-g]quinoxaline-4,9-diones and 2,3-Disubstituted-5,10-pyrazino[2,3-g]quinoxalinediones

  摘要：

  Series of 2-methyl-4,9-dihydro-1H-imidazo[4,5-g]quinoxaline-4,9-diones and 5,10-pyrazino[2,3g]quinoxalinediones have been synthesized from 6,7-dichloro-5,8-quinoxalinedione for developing new anticancer drugs. Intercalation complex of 2-methyl-4,9-dihydro-1-methyl-1H-imidazo-[4,5-g]quinoxaline-4,9-dione with GC/GC base pairs by a computer graphics-aided method was parallel to the axis of the helix. The interaction energies of synthetic compounds were low. 2-Methyl-4,9-dihydro-1-(4-bromophenyl)-1H-imidazo[4,5-g]quinoxaline-4,9-dione, which has the lowest interaction energy of the test compounds, was identified as being more cytotoxic against human gastric adenocarcinoma cells (MKN 45) than adriamycin and cis-platin in vitro using the MTT assay. The IC50 value of this compound was 1.30 mu M, whereas those of adriamycin and cis-platin were 3.13 and 86.5 mu M, respectively. The cytotoxicity of 2,3-diethyl-5,10-pyrazino-[2,3-g]quinoxalinedione was comparable to that of adriamycin in the in vitro assay. However these compounds showed loss of activity on human lung adenocarcinoma cells (PC 14) and human colon adenocarcinoma cells (colon 205). These results suggest that 2-methyl-4,9-dihydrol-(4-bromophenyl)-1H-imidazo[4,5-g]quinoxaline-4,9-dione, with the lowest interaction energy, might be an excellent and selective antitumor agent against MKN 45.

  DOI：

  10.1021/jm970695n
• 作为产物：
  描述：

  6,7-二氯喹喔啉-5,8-二酮 在 sodium azide 、 溶剂黄146 作用下， 反应 0.5h， 以90.4%的产率得到6-Azido-7-chloroquinoxaline-5,8-dione
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 2-Methyl-4,9-dihydro-1-substituted-1H-imidazo[4,5-g]quinoxaline-4,9-diones and 2,3-Disubstituted-5,10-pyrazino[2,3-g]quinoxalinediones

  摘要：

  Series of 2-methyl-4,9-dihydro-1H-imidazo[4,5-g]quinoxaline-4,9-diones and 5,10-pyrazino[2,3g]quinoxalinediones have been synthesized from 6,7-dichloro-5,8-quinoxalinedione for developing new anticancer drugs. Intercalation complex of 2-methyl-4,9-dihydro-1-methyl-1H-imidazo-[4,5-g]quinoxaline-4,9-dione with GC/GC base pairs by a computer graphics-aided method was parallel to the axis of the helix. The interaction energies of synthetic compounds were low. 2-Methyl-4,9-dihydro-1-(4-bromophenyl)-1H-imidazo[4,5-g]quinoxaline-4,9-dione, which has the lowest interaction energy of the test compounds, was identified as being more cytotoxic against human gastric adenocarcinoma cells (MKN 45) than adriamycin and cis-platin in vitro using the MTT assay. The IC50 value of this compound was 1.30 mu M, whereas those of adriamycin and cis-platin were 3.13 and 86.5 mu M, respectively. The cytotoxicity of 2,3-diethyl-5,10-pyrazino-[2,3-g]quinoxalinedione was comparable to that of adriamycin in the in vitro assay. However these compounds showed loss of activity on human lung adenocarcinoma cells (PC 14) and human colon adenocarcinoma cells (colon 205). These results suggest that 2-methyl-4,9-dihydrol-(4-bromophenyl)-1H-imidazo[4,5-g]quinoxaline-4,9-dione, with the lowest interaction energy, might be an excellent and selective antitumor agent against MKN 45.

  DOI：

  10.1021/jm970695n

文献信息

• Synthesis and Cytotoxicity of 2-Methyl-4,9-dihydro-1-substituted-1<i>H</i>-imidazo[4,5-<i>g</i>]quinoxaline-4,9-diones and 2,3-Disubstituted-5,10-pyrazino[2,3-<i>g</i>]quinoxalinediones
  作者：Hee-Won Yoo、Myung-Eun Suh、Sang Woo Park

  DOI：10.1021/jm970695n

  日期：1998.11.1

  Series of 2-methyl-4,9-dihydro-1H-imidazo[4,5-g]quinoxaline-4,9-diones and 5,10-pyrazino[2,3g]quinoxalinediones have been synthesized from 6,7-dichloro-5,8-quinoxalinedione for developing new anticancer drugs. Intercalation complex of 2-methyl-4,9-dihydro-1-methyl-1H-imidazo-[4,5-g]quinoxaline-4,9-dione with GC/GC base pairs by a computer graphics-aided method was parallel to the axis of the helix. The interaction energies of synthetic compounds were low. 2-Methyl-4,9-dihydro-1-(4-bromophenyl)-1H-imidazo[4,5-g]quinoxaline-4,9-dione, which has the lowest interaction energy of the test compounds, was identified as being more cytotoxic against human gastric adenocarcinoma cells (MKN 45) than adriamycin and cis-platin in vitro using the MTT assay. The IC50 value of this compound was 1.30 mu M, whereas those of adriamycin and cis-platin were 3.13 and 86.5 mu M, respectively. The cytotoxicity of 2,3-diethyl-5,10-pyrazino-[2,3-g]quinoxalinedione was comparable to that of adriamycin in the in vitro assay. However these compounds showed loss of activity on human lung adenocarcinoma cells (PC 14) and human colon adenocarcinoma cells (colon 205). These results suggest that 2-methyl-4,9-dihydrol-(4-bromophenyl)-1H-imidazo[4,5-g]quinoxaline-4,9-dione, with the lowest interaction energy, might be an excellent and selective antitumor agent against MKN 45.