2-methoxybenzo[b]phenazine-6,11-dione | 97977-64-5

• 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: 2-methoxybenzo[b]phenazine-6,11-dione
• 英文别名: 3-Methoxy-benzophenazin-6,11-chinon；2-Methoxy-6,11-dihydro-5,12-diazatetracene-6,11-dione；3-methoxybenzo[b]phenazine-6,11-dione
• CAS: 97977-64-5
• 化学式: C₁₇H₁₀N₂O₃
• mdl: MFCD14712375
• 分子量: 290.278
• InChiKey: ZCDVMDHAMKJSKU-UHFFFAOYSA-N

物化性质

• 沸点：
  520.7±45.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  69.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 在 sodium azide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 2-methoxybenzo[b]phenazine-6,11-dione
  参考文献：
  名称：

  Synthesis and cytotoxicity of 6,11-Dihydro-pyrido- and 6,11-Dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives

  摘要：

  6,11-Dihydro-pyrido[2,3-b]phenazine-6,11-diones and 6,11 -dihydro-benzo[2,3-b]phenazine-6,11-diones were synthesized from 6,7-dichloro-5,8-quinolinedione and 2,3-dichloro-1,4-naphthoquinone. The study on the cytotoxicity on these products revealed that the pyridophenazinediones, tetracyclic heteroquinone analogues with three nitrogen atoms exhibited a high cytotoxicity on several human tumor cell lines. Compound 9c and 9e showed in vitro antitumor activity comparable or superior to doxorubicin against the human ovarian tumor cells (SK-OV-3) and the human CNS cells (XF 498). The IC50 value for compound 9e,was 0.06 muM against the human CNS cells (XF 498), which was 2.6 times higher than that (0.16 muM) of doxorubicin. In addition, the X-ray crystallographic analysis of two phenazinedione derivatives (9b,c) showed clearly the exact position of the nucleophilic substitution of 6,7-dichloro-5,8-quinolinedione. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00028-2

文献信息

• Thermolysis of 2-azido-3-(R-anilino)-1,4-naphthoquinones. Nitrene insertion versus hydrogen abstraction
  作者：Silvia E. Loredo-Carrillo、Elisa Leyva、Matthew S. Platz、Agobardo Cárdenas-Chaparro、Antonio Martínez-Richa

  DOI：10.1016/j.tetlet.2020.151731

  日期：2020.4

  2-chloro-3-(R-anilino)-1,4-naphthoquinones react with sodium azide upon refluxing in DMF. The thermochemistry of 2-azido-3-(R-anilino)-1,4-naphthoquinone is strongly modified by the substituent on aniline. Having an strong electron-donor like O-R results in the generation of a phenazine while having an electron-withdrawing substituent results in the formation of 2-amino-3-(R-anilino)-1,4-naphthoquinone. The products obtained are explained in terms of singlet and/or triplet nitrene chemistry. (C) 2020 Elsevier Ltd. All rights reserved.
• Synthesis and cytotoxicity of 6,11-Dihydro-pyrido- and 6,11-Dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives
  作者：Young-Shin Kim、Se-Young Park、Hyun-Jung Lee、Myung-Eun Suh、Dieter Schollmeyer、Chong-Ock Lee

  DOI：10.1016/s0968-0896(03)00028-2

  日期：2003.4

  6,11-Dihydro-pyrido[2,3-b]phenazine-6,11-diones and 6,11 -dihydro-benzo[2,3-b]phenazine-6,11-diones were synthesized from 6,7-dichloro-5,8-quinolinedione and 2,3-dichloro-1,4-naphthoquinone. The study on the cytotoxicity on these products revealed that the pyridophenazinediones, tetracyclic heteroquinone analogues with three nitrogen atoms exhibited a high cytotoxicity on several human tumor cell lines. Compound 9c and 9e showed in vitro antitumor activity comparable or superior to doxorubicin against the human ovarian tumor cells (SK-OV-3) and the human CNS cells (XF 498). The IC50 value for compound 9e,was 0.06 muM against the human CNS cells (XF 498), which was 2.6 times higher than that (0.16 muM) of doxorubicin. In addition, the X-ray crystallographic analysis of two phenazinedione derivatives (9b,c) showed clearly the exact position of the nucleophilic substitution of 6,7-dichloro-5,8-quinolinedione. (C) 2003 Elsevier Science Ltd. All rights reserved.