7H-benzo[4,5]indolo[2,3-b]quinoxaline | 204-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7H-benzo[4,5]indolo[2,3-b]quinoxaline
• 英文别名: 7H-benzo[4,5]indolo[2,3-b]quinoxaline；benz[4,5]indolo[2,3-b]quinoxaline；Benz[4,5]indolo[2,3-b]chinoxalin；12,14,21-Triazapentacyclo[11.8.0.02,11.03,8.015,20]henicosa-1(21),2(11),3,5,7,9,13,15,17,19-decaene
• CAS: 204-96-6
• 化学式: C₁₈H₁₁N₃
• 分子量: 269.305
• InChiKey: NYTUCADCHHKZLF-UHFFFAOYSA-N

物化性质

• 沸点：
  571.4±30.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)
• 熔点：
  341-343 °C(Solv: N,N-dimethylformamide (68-12-2))

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7H-benzo[4,5]indolo[2,3-b]quinoxaline 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 2.17h， 生成 [2-(7H-benzo[4,5]indolo[2,3-b]quinoxalin-7-yl)ethyl]diethylamine
  参考文献：
  名称：

  Synthesis and biological activity of 7H-benzo[4,5]indolo[2,3-b]-quinoxaline derivatives

  摘要：

  New 7-(2-aminoethyl)-7H-benzo[4,5]indolo[2,3-b]quinoxalines (13-20) were synthesized with high yields starting from 3H-benzo[e]indole-1,2-dione. These compounds were screened for the cytotoxicity, anti-viral activity, interferon inducing ability and DNA affinity compared with the corresponding 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxaline derivatives (1-12). It was shown, that compounds 13-20 bind to DNA stronger (Ig K-a = 6.23-6.87) than compounds 1-12 (Ig K-a = 5.57-5.89). Anti-viral activity is significantly reduced with annulations of benzene ring in Indoloquinoxaline moiety 13-20. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.040
• 作为产物：
  描述：

  4,5-苯并靛红 、 邻苯二胺 在 溶剂黄146 作用下， 反应 2.0h， 生成 7H-benzo[4,5]indolo[2,3-b]quinoxaline
  参考文献：
  名称：

  Synthesis and biological activity of 7H-benzo[4,5]indolo[2,3-b]-quinoxaline derivatives

  摘要：

  New 7-(2-aminoethyl)-7H-benzo[4,5]indolo[2,3-b]quinoxalines (13-20) were synthesized with high yields starting from 3H-benzo[e]indole-1,2-dione. These compounds were screened for the cytotoxicity, anti-viral activity, interferon inducing ability and DNA affinity compared with the corresponding 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxaline derivatives (1-12). It was shown, that compounds 13-20 bind to DNA stronger (Ig K-a = 6.23-6.87) than compounds 1-12 (Ig K-a = 5.57-5.89). Anti-viral activity is significantly reduced with annulations of benzene ring in Indoloquinoxaline moiety 13-20. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.040

文献信息

• Hinsberg; Simcoff, Chemische Berichte, 1898, vol. 31, p. 253
  作者：Hinsberg、Simcoff

  DOI：——

  日期：——
• CHUPAXIN O. N.; POSTOVSKIJ I. YA.; SIDOROV E. O., DOKL. AN CCCP <DANK-AS>, 1975, 224, HO 2, 349-350
  作者：CHUPAXIN O. N.、 POSTOVSKIJ I. YA.、 SIDOROV E. O.

  DOI：——

  日期：——
• Synthesis and biological activity of 7H-benzo[4,5]indolo[2,3-b]-quinoxaline derivatives
  作者：Marina O. Shibinskaya、Alexander S. Karpenko、Sergey A. Lyakhov、Sergey A. Andronati、Nadezhda M. Zholobak、Nikolay Ya. Spivak、Natalia A. Samochina、Lev M. Shafran、Mykhail Ju. Zubritsky、Valerij F. Galat

  DOI：10.1016/j.ejmech.2010.11.040

  日期：2011.2

  New 7-(2-aminoethyl)-7H-benzo[4,5]indolo[2,3-b]quinoxalines (13-20) were synthesized with high yields starting from 3H-benzo[e]indole-1,2-dione. These compounds were screened for the cytotoxicity, anti-viral activity, interferon inducing ability and DNA affinity compared with the corresponding 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxaline derivatives (1-12). It was shown, that compounds 13-20 bind to DNA stronger (Ig K-a = 6.23-6.87) than compounds 1-12 (Ig K-a = 5.57-5.89). Anti-viral activity is significantly reduced with annulations of benzene ring in Indoloquinoxaline moiety 13-20. (C) 2010 Elsevier Masson SAS. All rights reserved.