4-氨基-3-溴-5-硝基吡啶 | 89284-05-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 4-氨基-3-溴-5-硝基吡啶
• 中文别名: 3-溴-4-氨基-5-硝基吡啶；4-氨基-3-硝基-5-溴吡啶
• 英文名称: 3-bromo-5-nitropyridin-4-amine
• CAS: 89284-05-9
• 化学式: C₅H₄BrN₃O₂
• mdl: MFCD01646057
• 分子量: 218.01
• InChiKey: UXDLBXRMNSJEPB-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175℃
• 沸点：
  346.5±37.0 °C(Predicted)
• 密度：
  1.929

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Amino-3-bromo-5-nitropyridine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Amino-3-bromo-5-nitropyridine
CAS number: 89284-05-9

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
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.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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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.
Store in closed vessels.
Storage:

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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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C5H4BrN3O2
Molecular weight: 218

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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：

  4-氨基-3-溴-5-硝基吡啶 在 吡啶 、 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 生成 N-isopropyl-N-[(7-nitro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]propan-2-amine
  参考文献：
  名称：

  铜催化的多米诺骨牌多组分偶联和环化反应可高效合成氨基甲基化的氮杂吲哚及其相应的吡咯稠合衍生物

  摘要：

  已经开发了通过多米诺铜催化的多组分偶联和环化合成氨基甲基化的氮杂吲哚衍生物的有效方法。使用各种仲胺和醛，将N-取代的3-乙炔基-4-氨基吡啶以中等至优异的产率转化为取代的氮杂吲哚。通过使用带有两个炔基的3，4-二氨基吡啶衍生物，通过可控的逐步环化合成相应的吡咯稠合的氮杂吲哚。

  DOI：

  10.1016/j.tet.2011.12.059
• 作为产物：
  描述：

  4-氨基-3-硝基吡啶 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 反应 48.0h， 以67%的产率得到4-氨基-3-溴-5-硝基吡啶
  参考文献：
  名称：

  铜催化的多米诺骨牌多组分偶联和环化反应可高效合成氨基甲基化的氮杂吲哚及其相应的吡咯稠合衍生物

  摘要：

  已经开发了通过多米诺铜催化的多组分偶联和环化合成氨基甲基化的氮杂吲哚衍生物的有效方法。使用各种仲胺和醛，将N-取代的3-乙炔基-4-氨基吡啶以中等至优异的产率转化为取代的氮杂吲哚。通过使用带有两个炔基的3，4-二氨基吡啶衍生物，通过可控的逐步环化合成相应的吡咯稠合的氮杂吲哚。

  DOI：

  10.1016/j.tet.2011.12.059

文献信息

• [EN] 3-(3H-IMIDAZO[4,5-C]PYRIDIN-2-YL)-1H-PYRAZOLO[4,3-B]PYRIDINES AND THERAPEUTIC USES THEREOF<br/>[FR] 3-(3H-IMIDAZO[4,5-C]PYRIDIN-2-YL)-1H-PYRAZOLO[4,3-B]PYRIDINES ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：SAMUMED LLC

  公开号：WO2017023988A1

  公开（公告）日：2017-02-09

  4-Azaindazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present invention concerns the use of a 4-azaindazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.

  披露了用于治疗各种疾病和病理的4-氮杂吲唑化合物。更具体地，本发明涉及使用4-氮杂吲唑化合物或其类似物，治疗通过Wnt途径信号激活所特征化的疾病（例如癌症、异常细胞增殖、血管生成、纤维化疾病、骨骼或软骨疾病和骨关节炎），调节由Wnt途径信号介导的细胞事件，以及由于Wnt途径和/或一个或多个Wnt信号组分的突变或失调而导致的遗传疾病和神经病理状况/障碍/疾病。还提供了治疗与Wnt相关疾病状态的方法。
• 1H-PYRAZOLO[3,4-B]PYRIDINES AND THERAPEUTIC USES THEREOF
  申请人：SAMUMED, LLC

  公开号：US20130296302A1

  公开（公告）日：2013-11-07

  Provided herein are compounds according to Formulas (I) or (II) and pharmaceutically acceptable salts thereof, and compositions comprising the same, for use in various methods, including treating cancer, abnormal cellular proliferation, angiogenesis, Alzheimer's disease, lung disease, osteoarthritis, idiopathic pulmonary fibrosis and neurological conditions/disorders/diseases.

  本文提供了根据化学式（I）或（II）提供的化合物及其药学上可接受的盐，以及包含它们的组合物，用于各种方法，包括治疗癌症、异常细胞增殖、血管生成、阿尔茨海默病、肺部疾病、骨关节炎、特发性肺纤维化和神经系统疾病/紊乱/疾病。
• [EN] 1H-PYRAZOLO[3,4-B]PYRIDINES AND THERAPEUTIC USES THEREOF<br/>[FR] 1H-PYRAZOLO[3,4-B]PYRIDINES ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：EPITHERIX LLC

  公开号：WO2011084486A1

  公开（公告）日：2011-07-14

  Provided herein are compounds according to Formula (I) and pharmaceutically acceptable salts thereof, and compositions comprising the same, for use in various methods, including treating cancers such as colon, ovarian, pancreatic, breast, liver, prostate and hematologic cancers.

  本文提供了按照式（I）的化合物及其药用盐，以及包含它们的组合物，用于各种方法，包括治疗结肠癌、卵巢癌、胰腺癌、乳腺癌、肝癌、前列腺癌和血液系统肿瘤。
• Identification of 2,4-Disubstituted Imidazopyridines as Hemozoin Formation Inhibitors with Fast-Killing Kinetics and <i>In Vivo</i> Efficacy in the <i>Plasmodium falciparum</i> NSG Mouse Model
  作者：André Horatscheck、Ana Andrijevic、Aloysius T. Nchinda、Claire Le Manach、Tanya Paquet、Lutete Peguy Khonde、Jean Dam、Kailash Pawar、Dale Taylor、Nina Lawrence、Christel Brunschwig、Liezl Gibhard、Mathew Njoroge、Janette Reader、Mariëtte van der Watt、Kathryn Wicht、Ana Carolina C. de Sousa、John Okombo、Keletso Maepa、Timothy J. Egan、Lyn-Marie Birkholtz、Gregory S. Basarab、Sergio Wittlin、Paul V. Fish、Leslie J. Street、James Duffy、Kelly Chibale

  DOI：10.1021/acs.jmedchem.0c01411

  日期：2020.11.12

  cardiotoxicity and were addressed through structure–activity and structure–property relationship studies. Pharmacokinetic properties were assessed in mice for compounds showing desirable in vitro activity, a selectivity window over cytotoxicity, and microsomal metabolic stability. Frontrunner compound 37 showed good exposure in mice combined with good in vitro activity against the malaria parasite, which translated

  一系列 2,4-二取代咪唑并吡啶源自 SoftFocus 激酶文库，是从针对人类疟疾寄生虫恶性疟原虫的高通量表型筛选中鉴定出来的。命中化合物显示出中等的无性血阶段活性。在先导优化过程中，标记了几个问题，例如对多重耐药 K1 菌株的交叉耐药性、体外细胞毒性和心脏毒性，并通过结构-活性和结构-性质关系研究得到解决。在小鼠中评估了化合物的药代动力学特性，这些化合物显示出理想的体外活性、细胞毒性的选择性窗口和微粒体代谢稳定性。领跑者化合物37在小鼠中显示出良好的暴露，并结合良好的体外抗疟原虫活性，这在恶性疟原虫NOD -scid IL-2Rγ无效（NSG）小鼠模型中转化为体内功效。初步机理研究表明抑制血红素形成是一种促成作用方式。
• 3-(3H-IMIDAZO[4,5-C]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-C]PYRIDINE AND THERAPEUTIC USES THEREOF
  申请人：Samumed, LLC

  公开号：US20160068548A1

  公开（公告）日：2016-03-10

  Azaindazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present invention concerns the use of an azaindazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.

  Azaindazole化合物用于治疗各种疾病和病理已经被披露。更具体地，本发明涉及使用azaindazole化合物或其类似物，治疗通过Wnt途径信号激活所表征的疾病（例如癌症、异常细胞增殖、血管生成、纤维化疾病、骨骼或软骨疾病和骨关节炎），调节由Wnt途径信号介导的细胞事件，以及由于Wnt途径的突变或失调和/或一个或多个Wnt信号传导组分的遗传疾病和神经病理状况/障碍/疾病。还提供了治疗与Wnt相关疾病状态的方法。