3-溴-5-硝基吲唑 | 67400-25-3

• 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 - 苯并吡唑类
• 中文名称: 3-溴-5-硝基吲唑
• 中文别名: 5-硝基-3-溴吲唑；3-溴-5-硝基-1H-吲唑
• 英文名称: 3-bromo-5-nitro-1H-indazole
• 英文别名: 3-bromo-5-nitroindazole；3-Brom-5-nitro-indazol；3-bromo-5-nitro-2H-indazole
• CAS: 67400-25-3
• 化学式: C₇H₄BrN₃O₂
• 分子量: 242.032
• InChiKey: SYTGRKBQTUKOAI-UHFFFAOYSA-N

物化性质

• 熔点：
  227-229
• 沸点：
  437.3±25.0 °C(Predicted)
• 密度：
  1.965±0.06 g/cm3(Predicted)
• pKa：
  9.53±0.40 (Predicted,Most Acidic Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 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：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
5-Nitro-3-bromoindazole
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.
5-Nitro-3-bromoindazole
Ingredient name:
CAS number: 67400-25-3

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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, refrigerated.

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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: C7H4BrN3O2
Molecular weight: 242

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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

反应信息

• 作为反应物：
  描述：

  3-溴-5-硝基吲唑 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 palladium on activated charcoal 、 氢气 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S)-N-[3-(4-fluorophenyl)-1H-indazol-5-yl]-3-methylsulfanylpyrrolidine-3-carboxamide
  参考文献：
  名称：

  Discovery of 3( S )-thiomethyl pyrrolidine ERK inhibitors for oncology

  摘要：

  Compound 5 (SCH772984) was identified as a potent inhibitor of ERK1/2 with excellent selectivity against a panel of kinases (0/231 kinases tested @ 100 nM) and good cell proliferation activity, but suffered from poor PK (rat AUC PK @10 mpk = 0 mu M h; F% = 0) which precluded further development. In an effort to identify novel ERK inhibitors with improved PK properties with respect to 5, a systematic exploration of sterics and composition at the 3-position of the pyrrolidine led to the discovery of a novel 3(S)-thiomethyl pyrrolidine analog 28 with vastly improved PK (rat AUC PK @10 mpk = 26 mu M h; F% = 70). (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.04.063
• 作为产物：
  描述：

  7-硝基吲唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以92.5%的产率得到3-溴-5-硝基吲唑
  参考文献：
  名称：

  一种N-吲唑取代硫脲类衍生物及其制备方法 和应用

  摘要：

  本发明公开了一种N‑吲唑取代硫脲类衍生物及其制备方法和应用，属于化学医药技术领域。硫脲类衍生物，是一系列同时含有1H‑吲唑环结构和不对称硫脲结构的化合物，均为未见文献报道的新型结构化合物。对本发明所公开的硫脲类衍生物的生物活性测试结果分析表明，该类化合物具有较好的抗氧化活性，清除率的平均值超出80％，其中，化合物12b，12c，12d和12h的清除率均高于90％，化合物12h对DPPH的清除活性IC50为0.14mg/mL。部分目标化合物还对疱疹病毒、牛痘病毒、呼吸道肠道病毒、Coxsackie病毒、Feline冠状疱疹病毒、HIV病毒等都有一定的抑制活性，其中，化合物12c和12n的抗病毒活性较高。本发明所设计合成的新化合物有望还有新的生物活性未得到阐明，可为新药研发提供一定的物质基础。

  公开号：

  CN105753841B

文献信息

• Methods for treating an inflammatory condition or inhibiting JNK
  申请人：——

  公开号：US20040127536A1

  公开（公告）日：2004-07-01

  This invention is generally directed to Indazole Derivatives having the following structure: 1 or pharmaceutically acceptable salt thereof, wherein R 1 , R 2 and A are as defined herein. Such compounds have utility in the treatment of a wide range of diseases and disorders that are responsive to JNK inhibition, such as an inflammatory disease or disorder. Thus, methods of treating such diseases and disorders are also disclosed, as are pharmaceutical compositions containing one or more compounds of the above compounds.

  这项发明通常涉及吲唑衍生物，具有以下结构： 1 或药用可接受的盐，其中R 1 ，R 2 和A如本文所述定义。这类化合物在治疗对JNK抑制剂有响应的广泛疾病和障碍，如炎症性疾病或障碍中具有用途。因此，还披露了治疗这些疾病和障碍的方法，以及包含一个或多个上述化合物的药物组合物。
• Indazole compounds, compositions thereof and methods of treatment therewith
  申请人：Bhagwat S. Shripad

  公开号：US20050009876A1

  公开（公告）日：2005-01-13

  This invention is generally directed to the use of Indazole Compounds for treating or preventing diseases associated with protein kinases, including tyrosine kinases, such as proliferative diseases, inflammatory diseases, abnormal angiogenesis and diseases related thereto, atherosclerosis, macular degeneration, diabetes, obesity, pain and others. The methods comprise the administration to a patient in need thereof of an effective amount of an indazole compound that inhibits, modulates or regulates tyrosine kinase signal transduction. Novel indazole compounds or pharmaceutically acceptable salt thereof are presented herein.

  这项发明通常涉及使用吲唑化合物来治疗或预防与蛋白激酶相关的疾病，包括酪氨酸激酶，诸如增殖性疾病、炎症性疾病、异常血管生成及其相关疾病、动脉硬化、黄斑变性、糖尿病、肥胖、疼痛等。这些方法包括向有需要的患者施用有效量的吲唑化合物，以抑制、调节或控制酪氨酸激酶信号转导。本文中提供了一种新型的吲唑化合物或其药用可接受的盐。
• Discovery of Novel Benzimidazole and Indazole Analogues as Tubulin Polymerization Inhibitors with Potent Anticancer Activities
  作者：Yichang Ren、Yuxi Wang、Gang Li、Zherong Zhang、Lingling Ma、Binbin Cheng、Jianjun Chen

  DOI：10.1021/acs.jmedchem.0c01837

  日期：2021.4.22

  Novel indazole and benzimidazole analogues were designed and synthesized as tubulin inhibitors with potent antiproliferative activities. Among them, compound 12b exhibited the strongest inhibitory effects on the growth of cancer cells with an average IC50 value of 50 nM, slightly better than colchicine. 12b exhibited nearly equal potency against both, a paclitaxel-resistant cancer cell line (A2780/T

  设计并合成了新型吲唑和苯并咪唑类似物，作为具有有效抗增殖活性的微管蛋白抑制剂。其中，化合物12b对癌细胞的生长表现出最强的抑制作用，平均IC 50值为50 nM，略高于秋水仙碱。12b对紫杉醇抗性癌细胞系（A2780 / T，IC 50 = 9.7 nM）和相应的亲代细胞系（A2780S，IC 50 = 6.2 nM）表现出几乎相等的效力，因此在体外有效克服了对紫杉醇的抗性。12b的晶体结构通过X射线晶体学分析，将与微管蛋白复合的化合物拆分至2.45Å分辨率，并确认其直接结合至秋水仙碱位点。此外，12b在黑素瘤肿瘤模型中显示出显着的体内抗肿瘤功效，肿瘤生长抑制率分别为78.70％（15 mg / kg）和84.32％（30 mg / kg）。总的来说，这项工作表明12b是一种有前途的铅化合物，作为潜在的抗癌剂值得进一步研究。
• [EN] SUBSTITUTED INDAZOLE COMPOUNDS, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH<br/>[FR] COMPOSÉS INDAZOLE SUBSTITUÉS , COMPOSITIONS LES CONTENANT ET MÉTHODES DE TRAITEMENT AU MOYEN DESDITS COMPOSÉS
  申请人：CELGENE CORP

  公开号：WO2016089977A1

  公开（公告）日：2016-06-09

  Provided herein are methods for treating and preventing malaria and/or Babesiosis, the methods comprising administering an effective amount of Indazole Compounds having the formulas: (I)[Formula (I) should be inserted here] or (II)[Formula (II) should be inserted here] wherein R1, R2, R3 and Y are as defined herein.

  提供的方法用于治疗和预防疟疾和/或巴贝虫病，这些方法包括施用有效量的吲唑化合物，其具有以下公式：(I) [在此处插入公式(I)]或(II) [在此处插入公式(II)]，其中R1、R2、R3和Y如本文所述定义。
• Indazole derivatives as JNK inhibitors and compositions and methods related thereto
  申请人：——

  公开号：US20020103229A1

  公开（公告）日：2002-08-01

  Compounds having activity as selective inhibitors of JNK are disclosed. The compounds of this invention are indazole derivatives having the following structure: 1 wherein R 1 , R 2 and A are as defined herein. Such compounds have utility in the treatment of a wide range of conditions that are responsive to JNK inhibition. Thus, methods of treating such conditions are also disclosed, as are pharmaceutical compositions containing one or more compounds of the above compounds.

  本发明公开了作为JNK选择性抑制剂的化合物。本发明的化合物是吲唑衍生物，具有以下结构： 1 其中R 1 ，R 2 和A如本文所述定义。此类化合物在治疗对JNK抑制产生响应的广泛病症方面具有用途。因此，还公开了治疗此类病症的方法，以及包含一个或多个上述化合物的药物组合物。

表征谱图