3,6-diamino-1,8-naphthalic anhydride | 126824-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,6-diamino-1,8-naphthalic anhydride
• 英文别名: 3,6-diamino-naphthalene-1,8-dicarboxylic acid-anhydride；3,6-Diamino-naphthalin-1,8-dicarbonsaeure-anhydrid；7,11-Diamino-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione
• CAS: 126824-57-5
• 化学式: C₁₂H₈N₂O₃
• 分子量: 228.207
• InChiKey: LFSRUKXWCXECLV-UHFFFAOYSA-N

物化性质

• 熔点：
  >450 °C
• 沸点：
  621.6±45.0 °C(Predicted)
• 密度：
  1.615±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,6-diamino-1,8-naphthalic anhydride 在 sodium iodide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 生成 N,N'-(1,3-dioxo-2-(2-(pyrrolidin-1-yl)ethyl)-2,3-dihydro-1H-benzo[de]isoquinoline-5,8-diyl)bis(3-(pyrrolidin-1-yl)propanamide)
  参考文献：
  名称：

  Design, synthesis, biophysical and biological studies of trisubstituted naphthalimides as G-quadruplex ligands

  摘要：

  A series of trisubstituted naphthalimides have been synthesized and evaluated as telomeric G-quadruplex ligands by biophysical methods. Affinity for telomeric G-quadruplex AGGG(TTAGGG)(3) binding was first screened by fluorescence titrations. Subsequently, the interaction of the telomeric G-quadruplex with compounds showing the best affinity has been studied by isothermal titration calorimetry and UV-melting experiments. The two best compounds of the series tightly bind the telomeric quadruplex with a 2:1 drug/DNA stoichiometry. These derivatives have been further evaluated for their ability to inhibit telomerase by a TRAP assay and their pharmacological properties by treating melanoma (M14) and human lung cancer (A549) cell lines with increasing drug concentrations. A dose-dependent inhibition of cell proliferation was observed for all cellular lines during short-term treatment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.062
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 3,6-diamino-1,8-naphthalic anhydride
  参考文献：
  名称：

  Dziewonski et al., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1936, vol. , p. 43,48

  摘要：

  DOI：