2-phenyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-phenyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione
• 英文别名: 2-phenyl-1H-anthra(1,2-d)imidazole-6,11-dione；2-phenyl-1H-anthra[1,2-d]imidazole-6,11-dione；2-phenyl-1H-anthra[2,1-d]imidazole-6,11-dione；2-phenyl-anthra[1,2-d]imidazole-6,11-dione；2-phenyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione；2-Phenyl-1(3)H-anthra[1,2-d]imidazol-6,11-dion；2-phenyl-3H-naphtho[3,2-e]benzimidazole-6,11-dione
• 化学式: C₂₁H₁₂N₂O₂
• 分子量: 324.338
• InChiKey: DONDWNNDTIOAET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 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：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-1-硝基蒽-9,10-二酮 在 sodium sulfide 作用下， 生成 2-phenyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione
  参考文献：
  名称：

  Schaarschmidt, Justus Liebigs Annalen der Chemie, 1915, vol. 407, p. 186

  摘要：

  DOI：

文献信息

• HETEROANNELATED ANTHRAQUINONE DERIVATIVES AND THE SYNTHESIS METHOD THEREOF
  申请人：HUANG Hsu-Shan

  公开号：US20090253707A1

  公开（公告）日：2009-10-08

  A heteroannelated anthraquinone derivative compound is provided. The heteroannelated anthraquinone derivative compound is represented by a formula (I): wherein R 1 is a substituent being one selected from a group consisting of i) a first substituent being one selected from a group consisting of a hydryl group, an amino group, a nitro group, a hydroxyl group and a cyan group, ii) a second substituent being one selected from a group consisting of (CH 2 ) n X, a straight (CH 2 ) n alkyl group, a (CH 2 ) n alkoxyl group, a branched (CH 2 ) n alkyl group, a C 3 ˜C 12 nephthenic group, and a C 3 ˜C 12 cyclic alkoxyl group, wherein 1=n=12, and X is a halogen, iii) a third substituent being one selected from a group consisting of a straight C 1 ˜C 8 alkyl group with a double-bond, a C 1 ˜C 8 alkoxyl group with a double-bond, a branched C 1 ˜C 8 alkyl group with a double-bond and a C 3 ˜C 8 nephthenic group with a double-bond, and iv) a fourth substituent of a C 5 ˜C 12 heterocyclic group.

  提供一个杂环化的蒽醌衍生物化合物，所述杂环化的蒽醌衍生物化合物由公式(I)表示： 其中R1是选自以下组中的取代基：i)第一取代基，选自包含羟基、氨基、硝基、羟基和氰基的组，ii)第二取代基，选自包含(CH2)nX、直链(CH2)n烷基、(CH2)n烷氧基、支链(CH2)n烷基、C3˜C12的环烷基和C3˜C12的环烷氧基的组，其中1≤n≤12，X是卤素，iii)第三取代基，选自包含直链C1˜C8的双键烷基、C1˜C8的双键烷氧基、支链C1˜C8的双键烷基和C3˜C8的双键环烷基的组，以及iv)第四取代基为C5˜C12的杂环基团。
• Synthesis, cytotoxicity and human telomerase inhibition activities of a series of 1,2-heteroannelated anthraquinones and anthra[1,2-d]imidazole-6,11-dione homologues
  作者：Hsu-Shan Huang、Tsung-Chih Chen、Ruei-Huei Chen、Kuo-Feng Huang、Fong-Chun Huang、Jing-Ru Jhan、Chun-Liang Chen、Chia-Chung Lee、Yang Lo、Jing-Jer Lin

  DOI：10.1016/j.bmc.2009.09.033

  日期：2009.11

  A series of 1,2-heteroannelated anthraquinones and anthra[1,2-d]imidazole-6,11-dione tetracyclic analogues with different side chain were prepared using an various synthetic route via acylation, cyclization, condensation, and intramolecular heterocyclization. Tetracyclic system containing alkyl and aryl, aromatic and heterocyclic, linear and cyclic, polar and apolar, and basic and acids residues were

  使用各种合成途径，通过酰化，环化，缩合和分子内杂环化，制备了一系列具有不同侧链的1,2-杂退火蒽醌和蒽[1,2 - d ]咪唑-6,11-二酮四环类似物。引入了包含烷基和芳基，芳族和杂环，线性和环状，极性和非极性以及碱性和酸性残基的四环体系。他们评估了它们对端粒酶活性，hTERT表达，细胞增殖以及对NCI 60细胞株人类肿瘤筛查的体外细胞毒性的影响。化合物4，11，12，14，15，16，17，19，20，23，25，和26是由NCI选择用于一个剂量筛选程序和进一步的研究4，23和25，其中曲线跨越这些线代表的内插值，以使50％生长抑制（GI 50），总生长抑制（TGI）和50％细胞杀伤率（LC 50）， 分别。进一步的研究未发现任何显示出对端粒酶抑制活性和hTERT抑制能力有效且显着的化合物。在NCI的筛选中对这些化合物进行的对比测试显示出不同的效力水平和不同的细胞毒性作用，显然与核心环
• Catalyst-free one-pot synthesis of benzimidazoles from 1,2-diaminoarenes and alcohols
  作者：Mahender Reddy Marri、Swamy Peraka、Arun Kumar Macharla、Naresh Mameda、Srujana Kodumuri、Narender Nama

  DOI：10.1016/j.tetlet.2014.09.081

  日期：2014.11

  A new and efficient protocol is described for the one-pot synthesis of benzimidazoles from a variety of aryl alcohols and 1,2-diaminoarenes. The yields were ranging from moderate to excellent. Moreover, the present method is utilizing alcohols instead of aldehydes and the reactions are carried out under solvent- and catalyst-free conditions, offering an environmentally benign process.

  描述了一种新的有效方案，用于从多种芳基醇和1,2-二氨基芳烃一锅合成苯并咪唑。产量从中等到极好。而且，本方法利用醇代替醛，并且反应在无溶剂和无催化剂的条件下进行，提供了对环境无害的方法。
• One-pot protocol for J-aggregated anthraimidazolediones catalyzed by phosphotungstic acid in PEG-400 under aerobic condition
  作者：Bhaswati Bhattacharyya、Arijit Kundu、Aniruddha Das、Kaliprasanna Dhara、Nikhil Guchhait

  DOI：10.1039/c5ra19190d

  日期：——

  A precise and productive one pot green protocol has been developed for the chemoselective synthesis of anthra[1,2-d]imidazole-6,11-diones using phosphotungstic acid (PTA) as a reusable catalyst on polyethylene glycol-400 (PEG-400) support under aerobic condition. It involves a simple synthetic procedure for a wide range of anthraimidazolediones from 1,2-diaminoanthraquinone and various aldehydes possessing

  已经开发出一种精确且高效的一锅绿色方案，用于蒽的化学选择性合成[1,2- d在有氧条件下，使用磷钨酸（PTA）作为可重复使用的催化剂在聚乙二醇-400（PEG-400）载体上使用]咪唑-6,11-二酮。它涉及一种简单的合成方法，可用于从1,2-二氨基蒽醌和具有π富集的芳族/杂芳族环和亲脂性烷基链的各种醛类中制备各种蒽咪唑二酮。在惰性气氛中，反应遵循不同的途径，从而产生独特的萘喹喔啉衍生物。合成的蒽咪唑二酮衍生物显示出受取代模式影响的不同自聚集形态。还观察到晶体堆积图案和具有J-聚集形态的光物理性质之间的良好协议。
• Specific Recognition and Sensing of CN⁻ in Sodium Cyanide Solution
  作者：Sukdeb Saha、Amrita Ghosh、Prasenjit Mahato、Sandhya Mishra、Sanjiv K. Mishra、E. Suresh、Satyabrata Das、Amitava Das

  DOI：10.1021/ol101281x

  日期：2010.8.6

  Specific recognition of CN− in sodium cyanide solution was achieved using two imidazole-based receptors (A and B). Visually detectable color changes were associated with the formation of hydrogen bonded adducts, A·CN− and B·CN−. Ratiometric fluorescence response was achieved for receptor A on binding to CN−, and this reagent was used for imaging bacterial cells pre-exposed to 1.42 μM CN− solution.

  CN的特异性识别-在氰化钠溶液中使用两种基于咪唑的受体（实现阿和乙）。视觉上可检测的颜色变化与形成氢键加合物的，相关联的A·CN -和乙·CN - 。比率荧光响应被用于受体实现阿上结合CN - ，和用于成像的细菌细胞预先暴露于1.42μMCN此试剂-溶液。