3-乙酰氨基萘-1,8-二羧酸酐 | 61690-44-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-乙酰氨基萘-1,8-二羧酸酐
• 英文名称: 3-acetamido-1,8-naphthalic anhydride
• 英文别名: 3-acetylaminonaphthalene-1,8-dicarboxylic anhydride；3-acetylamino-naphthalene-1,8-dicarboxylic acid-anhydride；3-Acetylamino-naphthalin-1,8-dicarbonsaeure-anhydrid；3-acetylamino-1,8-naphthalic acid anhydride；N-(2,4-dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-7-yl)acetamide
• CAS: 61690-44-6
• 化学式: C₁₄H₉NO₄
• 分子量: 255.23
• InChiKey: CVJMAWCKXRNOII-UHFFFAOYSA-N

物化性质

• 沸点：
  587.5±33.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 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：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-乙酰氨基萘-1,8-二羧酸酐 在 palladium on activated charcoal 硫酸 、 氢气 、 硝酸 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 74.0h， 生成 12-methyl-3-(2-pyrrolidin-1-ylethyl)-3,11,13-triazatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),11-hexaene-2,4-dione
  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
• 作为产物：
  描述：

  3-硝基-1,8-萘二甲酸酐 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、294.18 kPa 条件下， 反应 5.0h， 生成 3-乙酰氨基萘-1,8-二羧酸酐
  参考文献：
  名称：

  Synthesis and fluorescence ofN-substituted-1,8-naphthalimides

  摘要：

  AbstractA number of novel N‐substituted‐1,8‐naphthalimides have been prepared and their fluorescence yields measured in water at pH 7.4. The type of substitutent and the substitution pattern on the naphthalimide nucleus produce markedly different fluorescence yields, (quantum efficiencies, ø varying from ø = 0‐0037 for N‐(3‐N'‐morpholino‐1‐propyl)‐4‐amino‐3‐methoxy‐1,8‐naphthalirnide (7) to ø = 0–77 for N‐(3‐bromopropyl)‐4‐acetamido‐1,8‐naphthalimide (31).

  DOI：

  10.1002/jhet.5570230337

文献信息

• N(Aminoalkyl)-naphthalimides and their derivatives
  申请人：Laboratorios Made, S.A.

  公开号：US04204063A1

  公开（公告）日：1980-05-20

  N-substituted-3-substituted naphthalimides are prepared by reacting 3-substituted naphthalic acid with a compound having a primary amino group. The naphthalimides possess cytotoxic properties.

  N-取代-3-取代萘酰亚胺是通过将3-取代萘甲酸与具有一次氨基的化合物反应制备的。这些萘酰亚胺具有细胞毒性。
• Fernandez Brana; Martinez Sanz; Castellano, European Journal of Medicinal Chemistry, 1981, vol. 16, # 3, p. 207 - 212
  作者：Fernandez Brana、Martinez Sanz、Castellano、et al.

  DOI：——

  日期：——
• Bis-naphthalimides. 2. Synthesis and biological activity of 5,6-acenaphthalimidoalkyl-1,8-naphthalimidoalkyl amines
  作者：MF Braña、JM Castellano、M Morán、MJ Pérez de Vega、XD Qian、CA Romerdahl、G Keilhauer

  DOI：10.1016/0223-5234(96)88230-4

  日期：1995.1

  A series of non-symmetric bis-naphthalimides bearing a conveniently substituted 1,8-naphthalimide and a 5,6-acenaphthalimide chromophore was synthesized and in vitro activities were determined. Although previous studies suggested that the presence of the acenaphthalimide system in the structure enhances aqueous solubility, we found that these compounds were no more soluble or cytotoxic than the homologous symmetric series.
• Jankowski, Zdzislaw; Stolarski, Roland, Polish Journal of Chemistry, 1981, vol. 55, # 3, p. 555 - 564
  作者：Jankowski, Zdzislaw、Stolarski, Roland

  DOI：——

  日期：——
• Anselm; Zuckmayer, Chemische Berichte, 1899, vol. 32, p. 3290
  作者：Anselm、Zuckmayer

  DOI：——

  日期：——