2-(4-hydroxyphenyl)-1H-anthra[1,2-d]imidazole-6,11-dione | 942119-33-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(4-hydroxyphenyl)-1H-anthra[1,2-d]imidazole-6,11-dione
• 英文别名: 2-(4-hydroxyphenyl)-3H-naphtho[3,2-e]benzimidazole-6,11-dione
• CAS: 942119-33-7
• 化学式: C₂₁H₁₂N₂O₃
• 分子量: 340.338
• InChiKey: QNKQRHGAMGCRIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-1H-anthra[1,2-d]imidazole-6,11-dione 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.5h， 生成 2-[4-[3-(diethylamino)propoxy]phenyl]-3H-naphtho[3,2-e]benzimidazole-6,11-dione
  参考文献：
  名称：

  Synthesis, DNA Binding, and Leishmania Topoisomerase Inhibition Activities of a Novel Series of Anthra[1,2-d]imidazole-6,11-dione Derivatives

  摘要：

  Nine novel anthra[1,2-d]imidazole-6,11-diones, differing in their side chain, were synthesized. UV-vis spectroscopy and viscometric titrations of these molecules with duplex DNA were used to assess their binding with DNA. Five of the nine compounds showed high inhibition activity against topoisomerase I of Leishmania donovani, with the one bearing the tetrazole side chain exhibiting an IC50 - 1 mu M. The inhibition activities were not related with their DNA binding affinity and depended on the nature of the side chain.

  DOI：

  10.1021/jm0610604
• 作为产物：
  描述：

  1,2-二氨基蒽醌 、 对羟基苯甲醛 以 硝基苯 为溶剂， 以64%的产率得到2-(4-hydroxyphenyl)-1H-anthra[1,2-d]imidazole-6,11-dione
  参考文献：
  名称：

  通过GOx酶促反应基于硼蒽醌衍生物的高特异性葡萄糖荧光传感

  摘要：

  硼酸蒽醌o HAQB和p HAQB已被设计，并被证明可作为葡萄糖的荧光生物传感器。感官分子，ö HAQB，表现出了通过的GOx酶反应的特定葡萄糖感测。在这种贡献，的荧光变化ø HAQB合理对应于在硼酸的至羟基基于传感器的转化葡萄糖的由H浓度2 ö 2从葡萄糖与葡萄糖氧化酶的酶反应而产生。然后，我们的传感系统已成功应用于确定0.08–0.42 mM范围内的葡萄糖浓度。的检测限（LOD）o使用GOx酶探针进行葡萄糖检测的HAQB约为0.011 mM。

  DOI：

  10.1016/j.tet.2012.08.037

文献信息

• A smart ratiometric red fluorescent chemodosimeter for fluoride based on anthraquinone nosylate
  作者：Shweta Shweta、Ajit Kumar、Neeraj Neeraj、Sharad Kumar Asthana、K. K. Upadhyay

  DOI：10.1039/c7nj01575e

  日期：——

  A smart ratiometric red fluorescent chemodosimeter (AH) has been explored for specific detection of F⁻ with a lowest detection limit of 3.45 × 10⁻¹⁰ M. The sensing mechanism was worked out as fluoride-triggered deprotonation of imidazole accompanied by deprotection of the nosylate group.

  一种智能比率红色荧光化学传感器（AH）已被开发用于特异性检测F-，最低检测限为3.45×10^-10 M。传感机制是通过氟离子触发咪唑脱质子化反应，同时去保护基团来实现的。
• Synthesis and evaluation of quinonoid compounds against tumor cell lines
  作者：Eufrânio N. da Silva、Bruno C. Cavalcanti、Tiago T. Guimarães、Maria do Carmo F.R. Pinto、Igor O. Cabral、Cláudia Pessoa、Letícia V. Costa-Lotufo、Manoel O. de Moraes、Carlos K.Z. de Andrade、Marcelo R. dos Santos、Carlos A. de Simone、Marilia O.F. Goulart、Antonio V. Pinto

  DOI：10.1016/j.ejmech.2010.11.006

  日期：2011.1

  Thirty two compounds were synthesized in moderate to high yields and showed activity against cancer cells HL-60 (leukemia), MDA-MB435 (melanoma), HCT-8 (colon) and SF295 (central nervous system), with IC50 below 2 mu M for some compounds. The beta-lapachone-based 1,2,3-triazoles showed the best cytoxicity profile and emerge as promising anticancer prototypes. Insights about the reactive oxygen species (ROS) mechanism of anticancer action for some compounds were obtained by addition of 1-bromoheptane that deplete reduced glutathione (GSH) content and by using N-acetylcysteine that protects cells against apoptotic cellular death, as well by analysis of thiobarbituric acid reactive substances (TBARS) formation, and oxidative DNA damage after treatment detected by the comet assay with the bacterial enzymes formamidopyrimidine DNA-glycosylase (FPG) and endonuclease III (ENDOIII). (C) 2010 Elsevier Masson SAS. All rights reserved.
• Preferential recognition of zinc ions through a new anthraquinonoidal calix[4]arene
  作者：Har Mohindra Chawla、Richa Shukla、Shubha Pandey

  DOI：10.1016/j.tetlet.2012.03.096

  日期：2012.6

  A novel anthraquinonoidal calix[4]arene derivative was designed and synthesized for the preferential recognition of biologically important zinc in preference to prominently similar cadmium ions and other metal ions via quenching of fluorescence intensity. The stoichiometry of host guest complexation has been determined to be 1:1. The fluorescence changes associated with the recognition event may be attributed to the interaction of zinc ions with the nitrogenous functionality attached at the lower rim of calix[4]arene cavity which allows spatial disposition of the anthraquinonoid segments. (C) 2012 Published by Elsevier Ltd.