11-hydroxy-2-(hydroxymethyl)anthra[9,1-de][1,3]oxazin-7(2H)-one | 1489168-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 11-hydroxy-2-(hydroxymethyl)anthra[9,1-de][1,3]oxazin-7(2H)-one
• 英文别名: 3-Hydroxy-15-(hydroxymethyl)-14-oxa-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9(17),10,12-heptaen-8-one；3-hydroxy-15-(hydroxymethyl)-14-oxa-16-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9(17),10,12-heptaen-8-one
• CAS: 1489168-70-8
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: XKXLZCWWXRIGHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,8-二羟基蒽醌 、 C.I.酸性橙108 在 吡啶 、 copper(I) bromide 作用下， 以77%的产率得到11-hydroxy-2-(hydroxymethyl)anthra[9,1-de][1,3]oxazin-7(2H)-one
  参考文献：
  名称：

  Synthesis, cytotoxicity and DNA binding of oxoazabenzo[de]anthracenes derivatives in colon cancer Caco-2 cells

  摘要：

  New oxoazabenzo[de]anthracenes derivatives were synthesised and characterised. Their interactions with calf thymus DNA were studied by UV spectrophotometric analysis and a competitive ethidium bromide displacement assay. Cytotoxicity was determined by MIT assay, against colon adenocarcinoma (Caco-2 cells). Among all the oxoazabenzo[delanthracenes derivatives reported herein only the piperidino derivative exhibited strong DNA binding properties and cytotoxic activity with IC50 values in the range of 16 +/- 1.5 mu M (72-h treatment). In addition, the piperidino derivative did not directly inhibit topoisomerase I and topoisomerase II enzymes. The results confirm that the presence of the oxoazabenzoldelanthracenes together with the piperidino functionality is crucial in exerting DNA binding and cytotoxic properties, hence demonstrating promise as a chemical scaffold for further development of new anticancer agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.038

文献信息

• Optical and Electrochemical Properties of Anthraquinone Imine Based Dyes for Dye-Sensitized Solar Cells
  作者：Christian Prinzisky、Ingo Meyenburg、Andreas Jacob、Benjamin Heidelmeier、Fabian Schröder、Wolfram Heimbrodt、Jörg Sundermeyer

  DOI：10.1002/ejoc.201501309

  日期：2016.2

  coefficients of up to 101600 L mol–1 cm–1. In addition, the absorption maxima of the 1-hydroxy-9,10-anthraquinone imines appear in the range of 246 and 591 nm, at variance with the absorption maxima of the parent 1-hydroxy-9,10-anthraquinone. The cyclic voltammograms of all the compounds show multiple redox processes. In addition, the optical absorption and photoluminescence spectra of 3 show suppressed segregation

  通过 9,9-二甲氧基-10-蒽酮衍生物（13、18 和 23）与不同的主要芳香族化合物的缩合，合成了许多蒽醌亚胺（1-3、5-8）和一种蒽酮二胺（4）。胺，在苯并吖啶酮 7 的情况下，通过随后的光诱导 6 电环化。所有化合物均通过紫外/可见光谱、循环伏安法和 X 射线衍射进行了充分表征。XRD分析证明1、3和5的优选互变异构体具有9-氨基-1,10-蒽醌或1-羟基-9,10-蒽醌亚胺核。此外，通过 1-氨基-9,10-蒽醌与 3,5-二叔丁基苯基-邻苯醌反应合成氨基蒽醌 9 和吩恶嗪 10，得到的染料具有高达 101600 的高摩尔消光系数L mol–1 cm–1。此外，1-羟基-9,10-蒽醌亚胺的吸收最大值出现在246和591nm的范围内，与母体1-羟基-9,10-蒽醌的吸收最大值不同。所有化合物的循环伏安图都显示出多个氧化还原过程。此外，3 的光吸收和光致发光光谱表明介孔 TiO2