3-硝基-4-羟基-6-溴喹啉 | 853908-50-6

• 物质功能分类: 有机原料 - 杂环化合物
• 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
• 中文名称: 3-硝基-4-羟基-6-溴喹啉
• 中文别名: 6-溴-4-羟基-3-硝基喹啉；6-溴-3-硝基喹啉-4-醇
• 英文名称: 6-bromo-3-nitroquinolin-4-ol
• 英文别名: 6-bromo-4-hydroxy-3-nitroquinoline；3-nitro-4-hydroxy-6-bromoquinoline；6-Bromo-3-nitro-4-quinolinol；6-bromo-3-nitro-1H-quinolin-4-one
• CAS: 853908-50-6
• 化学式: C₉H₅BrN₂O₃
• mdl: MFCD09800413
• 分子量: 269.054
• InChiKey: AMKJVYOALDEARM-UHFFFAOYSA-N

物化性质

• 沸点：
  389.3±37.0 °C(Predicted)
• 密度：
  1.878±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
6-Bromo-3-nitro-4-quinolinol
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
6-Bromo-3-nitro-4-quinolinol
Ingredient name:
CAS number: 853908-50-6

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H5BrN2O3
Molecular weight: 269.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

6-溴-4-羟基-3-硝基喹啉盐属于喹啉类衍生物，具有一定的碱性。它可用作有机合成与农药化学的中间体，并可用于生物活性分子、药物分子以及农药的合成。

制备工艺

将10克6-溴-4-羟基-3-硝基喹啉前体化合物和4.1克乙酸钾（20.90毫摩尔，当量比为1.2）加入反应烧瓶中。随后向反应体系中添加适量的乙酸酐，混合物在120°C下搅拌反应2小时。反应结束后，冷却至室温并过滤沉淀。将沉淀用醋酸反复洗涤后再用水洗涤。最后，在真空条件下干燥所得沉淀即可得到目标产物6-溴-4-羟基-3-硝基喹啉。

反应信息

• 作为反应物：
  描述：

  3-硝基-4-羟基-6-溴喹啉 在 bis-triphenylphosphine-palladium(II) chloride 、 铁粉 、 sodium hydride 、 sodium carbonate 、 氯化铵 、 caesium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 N-(8-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-1-(6-(2-cyanopropan-2-yl)pyridin-3-yl)-3-methyl-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF SUBSTITUTED IMIDAZO[4,5-C]QUINOLINE COMPOUNDS, INTERMEDIATES AND POLYMORPHS THEREOF
  [FR] PROCÉDÉ POUR LA PRÉPARATION DE COMPOSÉS D'IMIDAZO[4,5-C]QUINOLINE SUBSTITUÉS, D'INTERMÉDIAIRES ET DE POLYMORPHES DE CEUX-CI

  摘要：

  本发明涉及一种制备取代咪唑并[4,5-c]喹啉化合物（如所述的化合物I的化合物）及其中间体的方法。本发明还涉及化合物I中包含的化合物的多晶形态及其在治疗增殖性疾病，特别是癌症中的应用。

  公开号：

  WO2015145369A1
• 作为产物：
  描述：

  5-[(4-溴苯基氨基)亚甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮 在 二苯醚 、 硝酸 作用下， 以 丙酸 为溶剂， 反应 2.25h， 生成 3-硝基-4-羟基-6-溴喹啉
  参考文献：
  名称：

  作为 PI3K/mTOR 双抑制剂的新型苯磺酰脲衍生物的设计、合成和生物学评价

  摘要：

  设计、合成了五个系列的新型苯磺酰脲衍生物，19a-d、20a-d、21a-d、22a-d 和 23a-d，带有 4-苯基氨基喹啉支架，并且它们对四种癌细胞系（HepG-2、 A549、PC-3 和 MCF-7) 进行了评估。大多数化合物对癌细胞系显示出中等的细胞毒性活性。构效关系（SAR）和药理学结果表明，4-氨基喹啉支架和苯磺酰脲支架的引入有利于抗肿瘤活性。此外，4-苯胺基部分的对甲氧基取代和苯磺酰脲的对卤素取代对不同系列的化合物有不同的影响。此外，

  DOI：

  10.3390/molecules23071553
• 作为试剂：
  描述：

  5-bromo-2-((2-nitrovinyl)amino)benzoic acid 、 potassium acetate 、 乙酸酐 在 溶剂黄146 、 3-硝基-4-羟基-6-溴喹啉 作用下， 反应 1.55h， 生成 3-硝基-4-羟基-6-溴喹啉
  参考文献：
  名称：

  1H-Imidazo[4,5-C]Quinoline Derivatives in the Treatment of Protein Kinase Dependent Diseases

  摘要：

  本发明涉及在蛋白激酶依赖性疾病治疗中使用咪唑喹啉及其盐，并用于制造用于治疗该类疾病的药物制剂，咪唑喹啉用于治疗蛋白激酶依赖性疾病，一种治疗该类疾病的方法，包括向温血动物尤其是人类施用咪唑喹啉，包括咪唑喹啉的药物制剂，特别是用于治疗蛋白激酶依赖性疾病的药物制剂，新型咪唑喹啉以及制备新型咪唑喹啉的方法。

  公开号：

  US20070213355A1

文献信息

• 咪唑酮类衍生物、其药物组合物和用途
  申请人：北京富龙康泰生物技术有限公司

  公开号：CN104411706B

  公开（公告）日：2016-11-16

  本申请涉及咪唑酮类化合物、其药学可接受的盐、溶剂化物、多晶形物或前药，还涉及包含上述物质的药物组合物和用于预防和治疗蛋白激酶相关性疾病如癌症、代谢疾病、心血管疾病等的用途。
• [EN] COMBINATION OF KINASE INHIBITORS AND USES THEREOF<br/>[FR] COMBINAISON D'INHIBITEURS DE KINASE ET SES UTILISATIONS
  申请人：INTELLIKINE LLC

  公开号：WO2014151147A1

  公开（公告）日：2014-09-25

  The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In yet another aspect, a method of inhibiting phosphorylation of both Akt (S473) and Akt (T308) in a cell is set forth. The present invention also provides a pharmaceutical kit effective for treating a disease condition associated with PI3 -kinase α and/or mTOR in a subject.

  本发明提供了一种治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的方法。另一方面，该发明提供了一种治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的方法。在另一个方面，提出了一种抑制细胞内Akt（S473）和Akt（T308）磷酸化的方法。本发明还提供了一种有效治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的药物套装。
• COMBINATION OF KINASE INHIBITORS AND USES THEREOF
  申请人：INTELLIKINE, LLC

  公开号：US20150030588A1

  公开（公告）日：2015-01-29

  The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or a receptor tyrosine kinase (RTK) in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase α and/or an RTK in a subject. In yet another aspect, a method of inhibiting phosphorylation of Akt (S473) in a cell is set forth.

  本发明提供了一种治疗与PI3-激酶a和/或受体酪氨酸激酶（RTK）有关的疾病状况的方法。另一方面，该发明提供了一种治疗与PI3-激酶α和/或受体酪氨酸激酶（RTK）有关的疾病状况的方法。另一方面，提出了一种抑制细胞中Akt（S473）磷酸化的方法。
• [EN] IMIDAZO [4,5-C]QUINOLINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF TUMORS AND/OR INFLAMMATION<br/>[FR] DÉRIVÉS D'IMIDAZO[4,5-C]QUINOLÉINE ET LEUR UTILISATION DANS LE TRAITEMENT DE TUMEURS ET/OU D'UNE INFLAMMATION
  申请人：PIRAMAL LIFE SCIENCES LTD

  公开号：WO2011001212A1

  公开（公告）日：2011-01-06

  The present invention provides the compounds of formula (I): (I) The present invention relates to imidazo[4,5-c]quinoline derivatives of formula (I), process for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases mediated by phosphatidylinositol-3-kinase (PBK) and/or mammalian target of rapamycin (mTOR) and/or tumor necrosis factor-α (TNF-oc) and/or interleukin-6 (IL-6), particularly in the treatment of cancer and inflammation.

  本发明提供了式(I)的化合物：(I) 本发明涉及式(I)的咪唑[4,5-c]喹啉衍生物，其制备方法，含有它们的药物组合物以及它们在治疗由磷脂酰肌醇-3-激酶（PI3K）和/或哺乳动物雷帕霉素靶标（mTOR）和/或肿瘤坏死因子-α（TNF-α）和/或白细胞介素-6（IL-6）介导的疾病中的应用，特别是在治疗癌症和炎症中的应用。
• IMIDAZO [4,5-C]QUINOLINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF TUMORS AND/OR INFLAMMATION
  申请人：Kumar Sanjay

  公开号：US20120108627A1

  公开（公告）日：2012-05-03

  The present invention provides the compounds of formula (I): The present invention relates to imidazo[4,5-c]quinoline derivatives of formula (I), process for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases mediated by phosphatidylinositol-3-kinase (PBK) and/or mammalian target of rapamycin (mTOR) and/or tumor necrosis factor-α (TNF-oc) and/or interleukin-6 (IL-6), particularly in the treatment of cancer and inflammation.

  本发明提供了如下公式(I)的化合物：本发明涉及公式(I)的咪唑[4,5-c]喹啉衍生物，其制备方法，含有它们的药物组合物以及它们在治疗由磷脂酰肌醇-3-激酶（PBK）和/或哺乳动物雷帕霉素靶标（mTOR）和/或肿瘤坏死因子-α（TNF-α）和/或白细胞介素-6（IL-6）介导的疾病中的应用，特别是在治疗癌症和炎症中的应用。