3-硝基苯并蒽酮 | 17117-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 3-硝基苯并蒽酮
• 英文名称: 3-nitrobenzanthrone
• 英文别名: 3-nitro-7H-benz[de]anthracen-7-one；3-NBA；3-nitrobenzo[b]phenalen-7-one
• CAS: 17117-34-9
• 化学式: C₁₇H₉NO₃
• 分子量: 275.263
• InChiKey: QAJOWHGESRCVLY-UHFFFAOYSA-N

物化性质

• 保留指数：
  490

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

毒理性

• 致癌物分类

国际癌症研究机构致癌物：3-硝基苯并蒽酮

IARC Carcinogenic Agent:3-Nitrobenzanthrone

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：2B组：可能对人类致癌

IARC Carcinogenic Classes:Group 2B: Possibly carcinogenic to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第105卷：（2013年）柴油和汽油发动机排气及一些硝基芳烃

IARC Monographs:Volume 105: (2013) Diesel and Gasoline Engine Exhausts and Some Nitroarenes

来源:International Agency for Research on Cancer (IARC)

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  3-硝基苯并蒽酮 在 硝酸 、 氯 、 硝基苯 、 三氯苯 作用下， 生成 3,9-二氯-7H-苯并[de]蒽-7-酮
  参考文献：
  名称：

  DE490989

  摘要：

  公开号：
• 作为产物：
  描述：

  3-nitro-7-oxo-7H-benz[de]anthracene-11-carboxylic acid 在 喹啉 、 铜 作用下， 生成 3-硝基苯并蒽酮
  参考文献：
  名称：

  230.乌尔曼法合成中观苯并蒽酮和蒽酮

  摘要：

  DOI：

  10.1039/jr9370001096

文献信息

• Synthesis and Characterization of Some Nitrobenzanthrones: Suspected New Mutagens in Atmospheric Environment
  作者：Hitomi Suzuki、Takeji Enya、Yoshiharu Hisamatsu

  DOI：10.1055/s-1997-1352

  日期：1997.11

  Five mononitro-, three dinitro- and one trinitrobenzanthrones have been synthesized by the modified Ullmann cross-coupling reaction between nitro-substituted 1-iodonaphthalene and methyl 2-iodo-benzoates, followed by the Friedel-Crafts ring closure of the resulting 2-(1-naphthyl)benzoic acid derivatives.

  通过改良的乌尔曼交叉耦合反应合成了五种单硝基、三种双硝基和一种三硝基苯蒽酮，这些反应是将硝基取代的1-碘萘与甲基2-碘苯甲酸酯进行反应，随后对生成的2-(1-萘基)苯甲酸衍生物进行弗里德尔-克拉夫茨环合。
• Reaction of Benzanthrone (7<i>H</i>-Benz[<i>d</i>,<i>e</i>]anthracen-7-one) with Nitrogen Dioxide Alone or in Admixture with Ozone. Implications for the Atmospheric Formation of Genotoxic 3-Nitrobenzanthrone
  作者：Takeji Enya、Hitomi Suzuki、Yoshiharu Hisamatsu

  DOI：10.1246/bcsj.71.2221

  日期：1998.9

  The reaction of benzanthrone (7H-benz[d,e]anthracen-7-one, 1) with nitrogen dioxide alone or in admixture with ozonized oxygen has been investigated in polar and nonpolar organic solvents at different temperatures. A remarkable change of product distribution was observed depending on the solvent employed; 3-nitrobenzanthrone (4) was the main product from the reaction in dichloromethane, while 2-nitrobenzanthrone

  苯并蒽酮 (7H-benz[d,e]anthracen-7-one, 1) 与二氧化氮单独或与臭氧化氧混合的反应已在极性和非极性有机溶剂中在不同温度下进行了研究。根据所使用的溶剂，观察到产物分布的显着变化；3-硝基苯蒽酮 (4) 是二氯甲烷中反应的主要产物，而 2-硝基苯蒽酮是四氯甲烷中的主要产物。发现加入质子酸或无机固体载体可促进反应，有利于前者硝基化合物的形成，而后者则以牺牲为代价。确定了所有主要产品。
• Dose-Dependent Response to 3-Nitrobenzanthrone Exposure in Human Urothelial Cancer Cells
  作者：Mario Pink、Nisha Verma、Anna Zerries、Simone Schmitz-Spanke

  DOI：10.1021/acs.chemrestox.7b00174

  日期：2017.10.16

  A product of incomplete combustion of diesel fuel, 3-nitrobenzanthrone (3-NBA), has been classified as a cancer-causing substance. It first gained attention as a potential urinary bladder carcinogen due to the presence of its metabolite in urine and formation of DNA adducts. The aim of the present study was to characterize the dose–response relationship of 3-NBA in human urothelial cancer cell line (RT4) exposed to concentrations ranging from 0.0003 μM (environmentally relevant) to 80 μM by utilizing toxicological and metabolomic approaches. We observed that the RT4 cells were capable of bioactivation of 3-NBA within 30 min of exposure. Activity measurements of various enzymes involved in the conversion of 3-NBA in RT4 cells demonstrated NAD(P)H:quinone oxidoreductase (NQO1) as the main contributor for its bioactivation. Moreover, cytotoxicity assessment exhibited an initiation of adaptive mechanisms at low dosages, which diminished at higher doses, indicating that the capacity of these mechanisms no longer suffices, resulting in increased levels of intracellular reactive oxygen species, reduced proliferation, and hyperpolarisation of the mitochondrial membrane. To characterize the underlying mechanisms of this cellular response, the metabolism of 3-NBA and metabolomic changes in the cells were analyzed. The metabolomic analysis of the cells (0.0003, 0.01, 0.08, 10, and 80 μM 3-NBA) showed elevated levels of various antioxidants at low concentrations of 3-NBA. However, at higher exposure concentrations, it appeared that the cells reprogrammed their metabolism to maintain the cell homeostasis via activation of pentose phosphate pathway (PPP).

  柴油不完全燃烧的产物3-硝基苯并蒽酮（3-NBA）已被列为致癌物质。由于其在尿液中的代谢产物和DNA加合物，它首次引起了人们对潜在膀胱癌的关注。本研究的目的是利用毒理学和代谢组学方法，研究3-NBA在暴露于浓度为0.0003 μM（环境相关浓度）至80 μM的人类尿路上皮癌细胞系（RT4）中的剂量反应关系。我们观察到，RT4细胞能够在暴露30分钟内对3-NBA进行生物活化。对RT4细胞中参与3-NBA转化过程的各种酶的活性测量表明，NAD（P）H：醌氧化还原酶（NQO1）是其生物活化的主要贡献者。此外，细胞毒性评估显示，在低剂量下，适应性机制开始启动，而在高剂量下，适应性机制减弱，表明这些机制的能力不再足够，导致细胞内活性氧水平增加，增殖减少，线粒体膜超极化。为了描述这种细胞反应的潜在机制，我们分析了3-NBA的代谢和细胞中的代谢组学变化。对细胞（0.0003、0.01、0.08、10和80 μM 3-NBA）的代谢组学分析表明，在低浓度的3-NBA中，各种抗氧化剂的水平升高。然而，在更高的
• Examen de la preuve dans la documentation sur l’anesthésie: enquête et évaluation des articles sur les céphalées obstétricales post-ponction durale
  作者：Peter T. -L. Choi、Saramin E. Galinski、Stefan Lucas、Lawrence Takeuchi、Alejandro R. Jadad

  DOI：10.1007/bf03020418

  日期：2002.1

  Purpose: To describe a bibliographic database on the literature of postdural puncture headache (PDPH) in the obstetrical population, to describe the research architecture in this field, and to evaluate the quality of case-control studies, cohort studies, and controlled clinical trials on PDPH.Methods: Computerized bibliographic searches, citation review, and hand searches were conducted to find all relevant citations on incidence, clinical course, prevention, or treatment of PDPH in parturients. The study design and topic(s) covered by each study were evaluated. Case-control studies and cohort studies were evaluated using the Quality Index; clinical trials were evaluated using the Jadad scale.Results: One hundred ninety-six relevant citations were published between 1949 and 1999. Research on PDPH has been increasing rapidly with the majority of studies published in the 1990's. Incidence and prevention were the focus of over half of all citations. Optimal study designs were infrequently utilized. The methodological quality was poor for observational studies (Quality Index 10/29) and clinical trials (Jadad scale 2/5).Conclusion: Although the amount of research on PDPH in parturients is increasing, use of optimal study designs and improvement in methodology is needed.
• Recherches sur les d�riv�s ?-amin�s de diff�rentes c�tones
  作者：Henri de Diesbach

  DOI：10.1002/hlca.194002301147

  日期：——