benzo[ j]phenanthridine-7,12-dione | 121709-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: benzo[ j]phenanthridine-7,12-dione
• 英文别名: Benzo[J]Phenanthridine-7,12-Dione
• CAS: 121709-53-3
• 化学式: C₁₇H₉NO₂
• 分子量: 259.264
• InChiKey: SLDGHYLJMSMWLM-UHFFFAOYSA-N

物化性质

• 熔点：
  186 °C
• 沸点：
  486.2±14.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzo[ j]phenanthridine-7,12-dione 、 乙酸酐 在 sodium acetate 、 锌 作用下， 生成 7,12-diacetoxy-benzo[j]phenanthridine
  参考文献：
  名称：

  Borsche, Justus Liebigs Annalen der Chemie, 1937, vol. 532, p. 127,134

  摘要：

  DOI：
• 作为产物：
  描述：

  2-bromo-3-(bromomethyl)-1,4-dimethoxynaphthalene 在 吡啶 、 ammonium cerium (IV) nitrate 、 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 28.5h， 生成 benzo[ j]phenanthridine-7,12-dione
  参考文献：
  名称：

  Straightforward palladium-mediated synthesis and biological evaluation of benzo[j]phenanthridine-7,12-diones as anti-tuberculosis agents

  摘要：

  In 1991, WHO recognized the resurgence of tuberculosis as a global health problem. Although modern chemotherapy is effective against the causative pathogen Mycobacterium tuberculosis, the current drug regimens have failed to eradicate the disease. The success of the pathogen, partially attributed to drug resistance, necessitates the development of novel anti-tuberculosis drugs. Benzo[j]phenanthridine-7,12-diones, tetracyclic derivatives of the natural product benz[g]isoquinoline-5,10-dione, were conveniently synthesized via palladium-catalyzed intramolecular cyclization of N-methanesulfonyl-3-bromo-2-(arylamino)methyl-1,4-naphthoquinones. Here we report on the bioactivity of eight benzo[j]phenanthridine-7,12-dione derivatives as candidate drug molecules against M. tuberculosis and on their cytotoxicity on C3A human hepatocytes. The strongest antimicrobial activity (as detected by growth inhibition of bacteria, using luminometry and BACTEC 460-TB) and lowest cytotoxicity was found for 3-methylbenzo [j]phenanthridine-7,12-dione 5e, which was also effective in targeting intracellular M. tuberculosis (in murine J774 macrophages) and was not genotoxic for C3A hepatocytes. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.033

文献信息

• Metallation of pyridines and quinolines in the presence of a remote carboxylate group. New syntheses of heterocyclic quinones
  作者：Anne-Sophie Rebstock、Florence Mongin、François Trécourt、Guy Quéguiner

  DOI：10.1039/b312723k

  日期：——

  2-(3- and 2-Pyridylcarbonyl)benzoic acids (2, 3), 2-(2-pyridylcarbonyl)thiophene-3-carboxylic acid (6), 2-(3-quinolylcarbonyl)benzoic acid (10), and most of the corresponding esters (compounds 1, 7 and 9) are readily synthesized and involved in a deprotonation–condensation sequence. Biologically active aza-anthraquinones such as benzo[g]isoquinoline-5,10-dione (2-azaanthraquinone, 4) and benzo[g]quinoline-5,10-dione (1-azaanthraquinone, 5) are prepared using the strategy. Extension to other heterocyclic quinones such as thieno[3,2-g]quinoline-4,9-dione (8) and benzo[j]phenanthridine-7,12-dione (11) is also investigated.

  2-(3-和2-吡啶羧基)苯甲酸（2，3）、2-(2-吡啶羧基)噻吩-3-羧酸（6）、2-(3-喹啉羧基)苯甲酸（10）及大多数对应的酯（化合物1、7和9）可以方便地合成，并涉及去质子化-缩合的反应序列。生物活性的氮杂蒽醌如苯并[g]异喹啉-5,10-二酮（2-氮杂蒽醌，4）和苯并[g]喹啉-5,10-二酮（1-氮杂蒽醌，5）也是采用该策略制备的。此外，还研究了扩展至其他杂环醌的可能性，如噻吩[3,2-g]喹啉-4,9-二酮（8）和苯并[j]苯anthridine-7,12-二酮（11）。
• Regiodivergent and short total synthesis of calothrixins
  作者：Dipakranjan Mal、Joyeeta Roy、Kumar Biradha

  DOI：10.1039/c4ob01309c

  日期：——

  The anionic annulation of MOM-protected furoindolone with 4-bromoquinoline followed by deprotection of the N-MOM group provides calothrixin B, whereas that with 3-bromoquinoline yields isocalothrixin B. The outcomes are explained by the divergence of the reaction mechanism from commonly perceived quinolyne intermediate. A sequence of addition–cyclization–elimination is proposed to account for the formation of calothrixin from 4-bromoquinoline.

  MOM保护的呋喃啶酮与4-溴喹啉的阴离子环加成反应，随后去保护N-MOM基团，得到福乐兴素B，而与3-溴喹啉的反应则生成同福乐兴素B。结果的差异可通过反应机制的不同于常见的喹啉中间体进行解释。提出一种加成-环化-消除的反应序列，以解释从4-溴喹啉形成福乐兴素的过程。
• Khanapure, Subhash P.; Biehl, Edward R., Heterocycles, 1988, vol. 27, # 11, p. 2643 - 2650
  作者：Khanapure, Subhash P.、Biehl, Edward R.

  DOI：——

  日期：——
• Novel organic electroluminescent compounds and organic electroluminescent device using the same
  申请人：Eum Sung Jin

  公开号：US20100033083A1

  公开（公告）日：2010-02-11

  Provided are novel organic electroluminescent compounds, and organic electroluminescent devices and organic solar cells employing the same. Specifically, the organic electroluminescent compounds according to the invention are characterized in that they are represented by Chemical Formula (1): wherein, A, B, C and D independently represent CR 5 or N, provided that A, B, C and D cannot represent CR 5 all at the same time. Since the organic electroluminescent compounds according to the invention have good luminous efficiency and excellent color purity and life property of material, OLED's having very good operation life can be manufactured therefrom.
• US8153279B2
  申请人：——

  公开号：US8153279B2

  公开（公告）日：2012-04-10