6-溴喹啉-3-羧酸乙酯 | 481054-89-1

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 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: 6-溴喹啉-3-羧酸乙酯
• 中文别名: 6-溴喹啉-3-甲酸乙酯
• 英文名称: ethyl 6-bromoquinoline-3-carboxylate
• CAS: 481054-89-1
• 化学式: C₁₂H₁₀BrNO₂
• 分子量: 280.121
• InChiKey: OYVUIUHFSQPCSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

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：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 6-bromoquinoline-3-carboxylate
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: Ethyl 6-bromoquinoline-3-carboxylate
CAS number: 481054-89-1

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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: C12H10BrNO2
Molecular weight: 280.1

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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

反应信息

• 作为反应物：
  描述：

  6-溴喹啉-3-羧酸乙酯 在 hydrazine hydrate 作用下， 以 甲醇 为溶剂， 生成 6-Bromoquinoline-3-carbohydrazide
  参考文献：
  名称：

  新型 6-Aryl-3-(quinolin-3-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 的设计、合成和分子对接研究抗菌剂

  摘要：

  摘要 设计并合成了一系列以 1,2,4-三唑并[3,4- b ][1,3,4]噻二嗪为核心的含喹啉稠合杂环化合物。新合成的衍生物通过 FTIR、1 H 和13 C NMR 以及 ESI 质谱进行了表征。所有化合物均对革兰氏阴性菌和革兰氏阳性菌表现出优异的活性（MIC < 4.5 μg/mL），部分化合物对金黄色葡萄球菌和大肠杆菌具有活性，MIC 值在 5.10 至 6.10 μg/mL 之间毫升。计算分子对接研究显示在 –7.34 至 –8.10 kcal/mol 范围内具有良好的结合分数，并且预测四种化合物对细菌 DNA 促旋酶 (2XCT) 显示出显着的亲和力。

  DOI：

  10.1134/s1070428022120144
• 作为产物：
  描述：

  1-(叠氮甲基)-4-溴苯 在 三氟甲磺酸 、 三氟化硼乙醚 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 3.0h， 生成 6-溴喹啉-3-羧酸乙酯
  参考文献：
  名称：

  的从芳基甲基叠氮化物2,4 -未取代的喹啉-3-羧酸乙酯的合成经由一个多米诺过程†

  摘要：

  描述了通过多米诺法方便地合成2，4-未取代的喹啉-3-羧酸乙酯。该合成使用芳基甲基叠氮化物作为前体，该前体经历酸促进的重排以产生N-芳基亚胺鎓离子。继加3-乙氧基丙烯酸乙酯，分子内亲电芳族取代，消除和随后的氧化，喹啉产物以中等至优异的产率获得。

  DOI：

  10.1039/c3ob27493d

文献信息

• SUBSTITUTED ACETYL-COA CARBOXYLASE INHIBITORS
  申请人：Dow Robert Lee

  公开号：US20120270893A1

  公开（公告）日：2012-10-25

  The invention provides a compound of Formula (I) or a pharmaceutically acceptable salt thereof; wherein G is R 1 , R 2 and R 3 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of an acetyl-CoA carboxylase enzyme(s) in an animal.

  该发明提供了公式（I）的化合物或其药用可接受的盐；其中G为R1，R2和R3如本文所述；其药用组合物；以及其在治疗由于抑制动物中乙酰辅酶A羧化酶而调节的疾病、症状或疾病中的用途。
• A One-Step Synthesis of 2,4-Unsubstituted Quinoline-3-carboxylic Acid Esters from <i>o</i>-Nitrobenzaldehydes
  作者：Hariharan Venkatesan、Frances M. Hocutt、Todd K. Jones、Michael H. Rabinowitz

  DOI：10.1021/jo100392x

  日期：2010.5.21

  straightforward and efficient one-step procedure for the synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters is described. The simple reductive cyclization is carried out by treating various substituted o-nitrobenzaldehydes with inexpensive, commercially available 3,3-diethoxypropionic acid ethyl ester and SnCl2·2H2O in refluxing ethanol.

  描述了一种简单，有效的一步法合成2,4-未取代的喹啉-3-羧酸乙酯的方法。通过在回流的乙醇中用廉价的可商购的3，3-二乙氧基丙酸乙酯和SnCl 2 ·2H 2 O处理各种取代的邻硝基苯甲醛来进行简单的还原环化。
• HETEROCYCLIC COMPOUNDS, THEIR PREPARATION AND THEIR USE AS MEDICAMENTS, IN PARTICULAR AS ANTI-ALZHEIMER AGENTS
  申请人：Marsais Francis

  公开号：US20090062279A1

  公开（公告）日：2009-03-05

  The invention is related to compound which comprises at least one radical C═Y, Y being O or S, and an oxidable and non protonable nitrogen atom N wherein the distance (d) between the at least one carbon atom of the radical group C═Y and the nitrogen atom, when oxidized, is comprised between 0.3 and 0.8 nanometers. The invention is related to new heterocyclic compounds defined by formula G, their preparation, to pharmaceutical compositions comprising them and to their use as therapeutic agents, particularly in the treatment of neurodegenerative or Alzheimer disease.

  本发明涉及一种化合物，其包含至少一个基团C═Y，其中Y为O或S，以及一个可氧化且不可质子化的氮原子N，其中在氧化时，基团C═Y的至少一个碳原子与氮原子之间的距离(d)在0.3至0.8纳米之间。本发明涉及由公式G定义的新杂环化合物及其制备方法，涉及包含它们的制药组合物以及它们在治疗神经退行性或阿尔茨海默病方面的用途。
• Substituted acetyl-coa carboxylase inhibitors
  申请人：Dow Robert Lee

  公开号：US08802688B2

  公开（公告）日：2014-08-12

  The invention provides a compound of Formula (I) or a pharmaceutically acceptable salt thereof; wherein G is R1, R2 and R3 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of an acetyl-CoA carboxylase enzyme(s) in an animal.

  本发明提供了一个公式(I)的化合物或其药学上可接受的盐；其中G为R1，R2和R3如本文所述；以及其药物组合物；和在治疗受到动物体内乙酰辅酶A羧化酶酶抑制调节的疾病、病状或障碍中使用的方法。
• Discovery and Optimization of Quinoline Analogues as Novel Potent Antivirals against Enterovirus D68
  作者：Xiaoyuan Li、Yuexiang Li、Shiyong Fan、Ruiyuan Cao、Xiaojia Li、Xiaomeng He、Wei Li、Longfa Xu、Tong Cheng、Honglin Li、Wu Zhong

  DOI：10.1021/acs.jmedchem.2c01311

  日期：2022.11.10

  diseases. However, there are no specific antiviral drugs or vaccines against EV-D68. Herein, through virtual screening and rational design, a series of novel quinoline analogues as anti-EV-D68 agents targeting VP1 were identified. Particularly, 19 exhibited potent antiviral activity with an EC50 value ranging from 0.05 to 0.10 μM against various EV-D68 strains and showed inhibition of viral replication

  肠道病毒D68（EV-D68）是一种非脊髓灰质炎肠道病毒，主要通过呼吸道传播，具有大规模传播的潜在威胁。EV-D68 感染主要引起儿童中度至重度呼吸道疾病，并可能诱发神经系统疾病。然而，没有针对 EV-D68 的特异性抗病毒药物或疫苗。在此，通过虚拟筛选和合理设计，确定了一系列新型喹啉类似物作为靶向 VP1 的抗 EV-D68 药物。特别是，19种表现出有效的抗病毒活性，EC为 50针对各种 EV-D68 菌株的值范围为 0.05 至 0.10 μM，并通过蛋白质印迹、免疫荧光和噬菌斑形成测定验证了对病毒复制的抑制作用。机理研究表明，抗 EV-D68 药物主要通过与 VP1 相互作用发挥作用。大鼠可接受的生物利用度为 23.9%，人肝微粒体的代谢稳定性显着（Cl int = 10.8 mL/min/kg，t 1/2 = 148 分钟）表明具有新型支架的化合物19值得进一步研究。