3-acetylamino-4-nitronaphthalene-1,8-dicarboxylic anhydride | 489430-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-acetylamino-4-nitronaphthalene-1,8-dicarboxylic anhydride
• 英文别名: N-(8-nitro-2,4-dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaen-7-yl)acetamide
• CAS: 489430-13-9
• 化学式: C₁₄H₈N₂O₆
• 分子量: 300.227
• InChiKey: GJSJOWPSSZDTBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-acetylamino-4-nitronaphthalene-1,8-dicarboxylic anhydride 在 10percent Pd/C 硫酸 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 3,4-diaminonaphthalene-1,8-dicarboxylic anhydride
  参考文献：
  名称：

  Synthesis, biological evaluation and DNA binding properties of novel mono and bisnaphthalimides

  摘要：

  我们合成了一系列新型的单萘二甲酰亚胺和双萘二甲酰亚胺，并评估了它们对三种肿瘤细胞系的抗增殖活性。双萘二甲酰亚胺 3 和 4 含有一个与萘二甲酰亚胺系统融合的吡嗪环，其活性约为 10-8 µM，与艾林萘胺相似。对一些活性最强的化合物的 DNA 结合特性和诱导 DNA 损伤的能力进行了研究。

  DOI：

  10.1039/b209042b
• 作为产物：
  描述：

  3-乙酰氨基萘-1,8-二羧酸酐 在 硫酸 、 硝酸 作用下， 反应 2.0h， 以62%的产率得到3-acetylamino-4-nitronaphthalene-1,8-dicarboxylic anhydride
  参考文献：
  名称：

  Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties of a New Series of Imidazonaphthalimides

  摘要：

  A series of mono and bisintercalators based on the 5,8-dihydrobenz [de]imidazo [4,5-g]isoquinoline-4,6-dione system were synthesized and evaluated for growth inhibitory properties in several human cell lines. All target compounds showed activity in the micromolar range. Representative compounds were evaluated using UV-vis spectroscopy and viscosimetric determinations, showing that they behave as DNA intercalators. Molecular modeling techniques were used in order to rationalize the moderate activity observed for bisnaphthalimides.

  DOI：

  10.1021/jm020950q

文献信息

• Synthesis, biological evaluation and DNA binding properties of novel mono and bisnaphthalimides
  作者：Miguel F. Braña、Mónica Cacho、Ana Ramos、M. Teresa Domínguez、Jose M. Pozuelo、Cristina Abradelo、M. Fernanda Rey-Stolle、Mercedes Yuste、Carolina Carrasco、Christian Bailly

  DOI：10.1039/b209042b

  日期：2003.2.11

  A novel series of mono and bisnaphthalimides was synthesized and their antiproliferative activities were evaluated against three tumor cell lines. Bisnaphthalimides 3 and 4, bearing a pyrazine ring fused to the naphthalimide system, showed activities in the order of 10−8 µM, similar to elinafide. DNA binding properties and the ability to induce DNA damage were studied for some of the most active compounds.

  我们合成了一系列新型的单萘二甲酰亚胺和双萘二甲酰亚胺，并评估了它们对三种肿瘤细胞系的抗增殖活性。双萘二甲酰亚胺 3 和 4 含有一个与萘二甲酰亚胺系统融合的吡嗪环，其活性约为 10-8 µM，与艾林萘胺相似。对一些活性最强的化合物的 DNA 结合特性和诱导 DNA 损伤的能力进行了研究。
• Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties of a New Series of Imidazonaphthalimides
  作者：Miguel F. Braña、Mónica Cacho、Mario A. García、Beatriz de Pascual-Teresa、Ana Ramos、Nuria Acero、Francisco Llinares、Dolores Muñoz-Mingarro、Cristina Abradelo、María Fernanda Rey-Stolle、Mercedes Yuste

  DOI：10.1021/jm020950q

  日期：2002.12.1

  A series of mono and bisintercalators based on the 5,8-dihydrobenz [de]imidazo [4,5-g]isoquinoline-4,6-dione system were synthesized and evaluated for growth inhibitory properties in several human cell lines. All target compounds showed activity in the micromolar range. Representative compounds were evaluated using UV-vis spectroscopy and viscosimetric determinations, showing that they behave as DNA intercalators. Molecular modeling techniques were used in order to rationalize the moderate activity observed for bisnaphthalimides.