4-氨基-7-氯喹啉 | 1198-40-9

• 物质功能分类: 化学试剂 - 有机试剂
• 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: 4-氨基-7-氯喹啉
• 英文名称: 4-amino-7-chloroquinoline
• 英文别名: 7-chloroquinolin-4-amine；7-chloro-4-aminoquinoline；7-Chlor-4-aminochinolin；(7-chloroquinolin-4-yl)-amine
• CAS: 1198-40-9
• 化学式: C₉H₇ClN₂
• mdl: MFCD00828822
• 分子量: 178.621
• InChiKey: NDRZSRWMMUGOBP-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152.5 °C
• 沸点：
  366.8±27.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 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：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 危险类别码：
  R14,R40,R36,R34,R25
• 危险品运输编号：
  UN 3265 8/PG 2
• WGK Germany：
  2
• RTECS号：
  RR4584700
• 海关编码：
  29420000
• 危险类别：
  4.1
• 安全说明：
  S22,S23,S24/25,S26,S36/37/39,S45
• 包装等级：
  II
• 危险性防范说明：
  P301+P310,P305+P351+P338
• 危险性描述：
  H301,H319
• 储存条件：
  应存放在2-8℃的环境中，避免光照，并在惰性气体保护下保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Amino-7-chloroquinoline
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H319: Causes serious eye irritation
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Amino-7-chloroquinoline
CAS number: 1198-40-9

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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
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H7ClN2
Molecular weight: 178.6

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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 chloride.

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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
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (4-Amino-7-chloroquinoline)

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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

4-氨基-7-氯喹啉是一种氨基喹啉，能够与铁原卟啉IX（Fe（III）PPIX）形成络合物，并抑制后者转化为β-血红素（血红蛋白）。

反应信息

• 作为反应物：
  描述：

  4-氨基-7-氯喹啉 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Inhibitors of Jak protein kinase

  摘要：

  本发明涉及用作蛋白激酶抑制剂的化合物。本发明还提供了包括所述化合物的药学上可接受的组合物以及使用该组合物治疗各种疾病、状况或障碍的方法。

  公开号：

  US20040038992A1
• 作为产物：
  描述：

  7-chloro-2,3-dihydro-1H-quinolin-4-one; hydrochloride 在 氨 、 苯酚 作用下， 生成 4-氨基-7-氯喹啉
  参考文献：
  名称：

  Bechli, Doklady Akademii Nauk SSSR, 1955, vol. 101, p. 679,682

  摘要：

  DOI：

文献信息

• Microwave-assisted synthesis of 4-quinolylhydrazines followed by nickel boride reduction: a convenient approach to 4-aminoquinolines and derivatives
  作者：Sandra Gemma、Gagan Kukreja、Pierangela Tripaldi、Maria Altarelli、Matteo Bernetti、Silvia Franceschini、Luisa Savini、Giuseppe Campiani、Caterina Fattorusso、Stefania Butini

  DOI：10.1016/j.tetlet.2008.01.128

  日期：2008.3

  Nickel(II) chloride/sodium borohydride combination was employed for the reduction of 4-hydrazinoquinoline derivatives to the corresponding anilines. This reductive protocol was efficiently applied for the reductive cleavage of monosubstituted hydrazines. We described herein the microwave-assisted synthesis of 4-hydrazinoquinolines, which furnished a high yielding and rapid two-step procedure for the

  氯化镍（II）/硼氢化钠组合用于将4-肼基喹啉衍生物还原为相应的苯胺。该还原方案被有效地应用于单取代肼的还原裂解。我们在本文中描述了4-肼基喹啉的微波辅助合成，其提供了高产率和快速的两步法，用于在温和条件下合成4-氨基喹啉作为抗疟原体。
• [EN] SUBSTITUTED QUINOLINE CCR5 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR CCR5 A BASE DE QUINOLEINE SUBSTITUES
  申请人：SCHERING AG

  公开号：WO2004002960A1

  公开（公告）日：2004-01-08

  The present invention relates to CCR5 receptor antagonists of formulae (1a) or (1b), enantiomers, diastereomers, salts and solvates thereof wherein R1, R2, R3, R4, R5, and R7 are as defined herein. The invention further includes a method of CCR5-mediated disorders employing such compounds.

  本发明涉及式（1a）或（1b）的CCR5受体拮抗剂，其对映体、二对映体、盐和溶剂合物，其中R1、R2、R3、R4、R5和R7如本文所定义。该发明还包括一种利用这些化合物治疗CCR5介导的疾病的方法。
• New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model
  作者：Jelena Konstantinović、Erkan Kiris、Krishna P. Kota、Johanny Kugelman-Tonos、Milica Videnović、Lisa H. Cazares、Nataša Terzić Jovanović、Tatjana Ž. Verbić、Boban Andjelković、Allen J. Duplantier、Sina Bavari、Bogdan A. Šolaja

  DOI：10.1021/acs.jmedchem.7b01710

  日期：2018.2.22

  The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative

  描述了使用基于体外HPLC的酶法测定各种甾体，苯并噻吩，噻吩和金刚烷4-氨基喹啉衍生物对A型肉毒杆菌神经毒素轻链（BoNT / A LC）的合成和抑制能力。另外，评估了化合物在小鼠胚胎干细胞衍生的运动神经元中对BoNT / A全毒素的活性。甚至在中毒后30分钟给药，类固醇衍生物16也显示出显着的保护作用（高达89％的未裂解SNAP-25）。这似乎是LC抑制剂在暴露后模型中拮抗小鼠胚胎干细胞衍生的运动神经元（mES-MNs）中BoNT中毒的第一个例子。口服16 高达600 mg / kg，qd的小鼠具有良好的耐受性，尽管在该剂量下未达到足够的未结合药物水平，但体外ADMET的良好结果有力地支持了该系列的进一步工作。
• Novel cinnamic acid/4-aminoquinoline conjugates bearing non-proteinogenic amino acids: Towards the development of potential dual action antimalarials
  作者：Bianca C. Pérez、Cátia Teixeira、Marta Figueiras、Jiri Gut、Philip J. Rosenthal、José R.B. Gomes、Paula Gomes

  DOI：10.1016/j.ejmech.2012.05.022

  日期：2012.8

  A series of cinnamic acid/4-aminoquinoline conjugates conceived to link, through a proper retro-enantio dipeptide, a heterocyclic core known to prevent hemozoin formation, to a trans-cinnamic acid motif capable of inhibiting enzyme catalytic Cys residues, were synthesized as potential dual-action antimalarials. The effect of amino acid configuration and the absence of the dipeptide spacer were also

  合成了一系列肉桂酸/ 4-氨基喹啉共轭物，它们通过适当的逆对映体二肽（一种已知可防止血红蛋白形成的杂环）连接至能够抑制酶催化Cys残基的反式肉桂酸基序。双重作用的抗疟药。还评估了氨基酸构型的影响和二肽间隔子的缺失。用其天然的L对应物替代D-氨基酸会导致抗疟原虫和falcipain抑制活性均下降，这表明前者是可取的。与这样的间隔分子是活性抗血液阶段疟原虫，在体外，和血红蛋白的形成，这暗示二肽在介导这两个活性中具有关键作用。反过来，不带间隔基的化合物则是更好的falcipain-2抑制剂，这可能是因为这些化合物较小，并且其乙烯基键更靠近催化Cys，如分子模型计算所表明的那样。这些新颖的结合物构成了针对针对血液阶段疟疾寄生虫的新型抗疟原虫的开发的有前途的线索。
• [EN] SMALL MOLECULE INHIBITORS OF AUTOPHAGY AND HISTONE DEACTYLASES AND USES THEREOF<br/>[FR] INHIBITEURS À PETITES MOLÉCULES D'AUTOPHAGIE ET D'HISTONE DÉSACÉTYLASE ET LEURS UTILISATIONS
  申请人：UNIV ARIZONA

  公开号：WO2021087077A1

  公开（公告）日：2021-05-06

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quinoline or thioxanthenone (or similar) structure which function as autophagy inhibitors and/or histone deactylase inhibitors, and their use as therapeutics for the treatment of conditions characterized with aberrant autophagy activity and/or aberrant HDAC activity (e.g., cancer, pulmonary hypertension, diabetes, neurodegenerative disorders, aging, heart disease, rheumatoid arthritis, infectious diseases, conditions and symptoms caused by a viral infection (e.g., COVID-19)).

  这项发明属于药物化学领域。特别是，该发明涉及一类新的小分子，具有喹啉或噻吨酮（或类似）结构，可作为自噬抑制剂和/或组蛋白脱乙酰酶抑制剂发挥作用，并用作治疗以异常自噬活性 和/或异常HDAC活性（例如，癌症、肺动脉高压、糖尿病、神经退行性疾病、衰老、心脏病、类风湿性关节炎、感染性疾病、病毒感染（例如，COVID-19）引起的状况和症状）为特征的疾病的治疗方法。