7-溴-4-羟基喹啉-3-甲酸乙酯 | 179943-57-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 7-溴-4-羟基喹啉-3-甲酸乙酯
• 中文别名: 4-羟基-7-溴喹啉-3-羧酸乙酯；7-溴-4-羟基-3-喹啉羧酸乙酯；4-羟基-7-溴-3-喹啉甲酸乙酯
• 英文名称: ethyl 7-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate
• 英文别名: 7-bromo-3-(ethoxycarbonyl)quinoline-4(1H)-one；ethyl 7-bromo-4-oxo-1H-quinoline-3-carboxylate
• CAS: 179943-57-8
• 化学式: C₁₂H₁₀BrNO₃
• mdl: MFCD00487280
• 分子量: 296.12
• InChiKey: WJFBKTAITAHHAR-UHFFFAOYSA-N

物化性质

• 熔点：
  307-309 °C
• 沸点：
  385.5±37.0 °C(Predicted)
• 密度：
  1.593±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  55.4
• 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：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 7-bromo-4-hydroxyquinoline-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 7-bromo-4-hydroxyquinoline-3-carboxylate
CAS number: 179943-57-8

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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: C12H10BrNO3
Molecular weight: 296.1

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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：

  7-溴-4-羟基喹啉-3-甲酸乙酯 在 sodium tetrahydroborate 、 水 、 potassium carbonate 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 7-bromo-1-methyl-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS HAVING INHIBITORY ACTIVITY AGAINST GLUCOSYLCERAMIDE SYNTHASE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PROCESSES FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  [FR] NOUVEAUX COMPOSÉS AYANT UNE ACTIVITÉ INHIBITRICE CONTRE LA GLUCOSYLCÉRAMIDE SYNTHASE OU SEL PHARMACEUTIQUEMENT ACCEPTABLE DE CEUX-CI, LEURS PROCÉDÉS DE PRÉPARATION, ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT

  摘要：

  本发明提供了一种具有色烷、异色烷、硫色烷或四氢喹啉基团的新化合物或其药用可接受盐，其制备方法，包含该化合物的药物组合物及其用途。具有色烷、异色烷、硫色烷或四氢喹啉基团或其药用可接受盐的化合物对葡萄糖基鞘氨醇合酶（GCS）具有抑制作用，因此可有益地应用于预防或治疗与GCS相关的各种疾病，如戈谢病、法布里病、泰萨病、帕金森病等。

  公开号：

  WO2021096241A1
• 作为产物：
  描述：

  乙氧基甲叉丙二酸二乙酯 在 二苯醚 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 7-溴-4-羟基喹啉-3-甲酸乙酯
  参考文献：
  名称：

  3-（苯并[d]噻唑-2-基）-4-氨基喹啉衍生物通过DNA嵌入作为新型支架拓扑异构酶I抑制剂：设计，合成和抗肿瘤活性

  摘要：

  已经设计并合成了二十七个3-（苯并[ d ]噻唑-2-基）-4-氨基喹啉衍生物作为拓扑异构酶I抑制剂。在体外针对四种人类肿瘤细胞系（MGC-803，人肝癌HepG-2，T24，和NCI-H460）和一个正常细胞系的抗增殖评价（HL-7702）表示，其中大部分表现出强的细胞毒性。其中，5a被认为是最有前途的候选物，其IC 50值低至约2.20±0.14，并被选作进一步探索。光谱分析和琼脂糖凝胶电泳分析表明5a可以与DNA相互作用并强烈抑制拓扑异构酶I（Topo I）。进一步筛选化合物5b的Topo I活性，5c，5e，5f，5h，5i，5j，5l和5n表明一些化合物可能与5a具有完全不同的细胞毒性。分子建模研究证实5a采用独特的模式与DNA和Topo I相互作用。其他分子机理研究表明，用5a处理MGC-803细胞可诱导S期阻滞，上调促凋亡蛋白，下调抗凋亡蛋白，激活caspase-3，随后诱导

  DOI：

  10.1039/c9nj05846j

文献信息

• HETEROCYCLIC UREA DERIVATIVES AND METHODS OF USE THEREOF
  申请人：CHOY Allison Laura

  公开号：US20100317624A1

  公开（公告）日：2010-12-16

  Compounds of formula (IA) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

  公式（IA）的化合物及其药用可接受的盐被描述。还描述了它们的制备过程、含有它们的药物组合物、它们作为药物的使用以及它们在治疗细菌感染中的用途。
• Synthesis and photodynamic effects of new porphyrin/4-oxoquinoline derivatives in the inactivation of S. aureus
  作者：Fernanda Savacini Sagrillo、Cristina Dias、Ana T. P. C. Gomes、Maria A. F. Faustino、Adelaide Almeida、Alan Gonçalves de Souza、Amanda Rodrigues Pinto Costa、Fernanda da Costa Santos Boechat、Maria Cecília Bastos Vieira de Souza、Maria G. P. M. S. Neves、José A. S. Cavaleiro

  DOI：10.1039/c9pp00102f

  日期：2019.8

  New porphyrin/4-oxoquinoline conjugates were synthesized from the Heck coupling reaction of a β-brominated porphyrin with 1-allyl-4-oxoquinoline derivatives, followed by demetallation and deprotection affording the promising photosensitizers 9a–e. Singlet oxygen studies have demonstrated that all the porphyrin/4-oxoquinoline conjugates 9a–e were capable of producing cytotoxic species and found to be

  β-溴化卟啉与1-allyl-4-oxoquinoline衍生物的Heck偶联反应合成了新的卟啉/ 4-氧喹啉共轭物，然后进行脱金属和脱保护，从而提供了有前途的光敏剂9a-e。单重态氧研究表明，所有卟啉/ 4-氧喹啉共轭物9a-e均能产生细胞毒性物质，并被认为是通过抗菌光动力疗法（aPDT）灭活金黄色葡萄球菌的极佳光敏剂。
• Fluorine walk: The impact of fluorine in quinolone amides on their activity against African sleeping sickness
  作者：Michael Berninger、Christine Erk、Antje Fuß、Joseph Skaf、Ehab Al-Momani、Ina Israel、Martina Raschig、Paul Güntzel、Samuel Samnick、Ulrike Holzgrabe

  DOI：10.1016/j.ejmech.2018.04.055

  日期：2018.5

  Human African Trypanosomiasis, also known as African sleeping sickness, is caused by the parasitic protozoa of the genus Trypanosoma. If there is no pharmacological intervention, the parasites can cross the blood-brain barrier (BBB), inevitably leading to death of the patients. Previous investigation identified the quinolone amide GHQ168 as a promising lead compound having a nanomolar activity against

  人类非洲锥虫病，也称为非洲昏睡病，是由锥虫属的寄生原生动物引起的。如果没有药理学干预，这些寄生虫会穿过血脑屏障（BBB），不可避免地导致患者死亡。先前的研究确定喹诺酮酰胺GHQ168是一种有前途的对T. b具有纳摩尔活性的先导化合物。布鲁西。在这里，关于毒性，药代动力学和抗胰锥虫活性，研究了氟取代在不同位置的作用。这种“氟走”导致了新化合物具有更好的代谢稳定性和对T的一致活性。布鲁西。
• Substituted benzyl pyrimidines
  申请人：Hoffmann-La Roche Inc.

  公开号：US05763450A1

  公开（公告）日：1998-06-09

  Compounds of the formula: ##STR1## in which R.sup.1 is lower alkoxy, R.sup.2 is bromine or lower alkoxy, and R.sup.3 is aryl, heteroaryl or a group --Q--R.sup.30, wherein Q is ethylene, vinylene or ethynylene and R.sup.30 is aryl, heteroaryl, lower alkoxycarbonyl or carbamoyl; hydrolyzable esters of carboxylic acids of formula I; and pharmaceutically acceptable salts of these compounds are useful for treating infectious diseases.

  公式为：##STR1## 其中 R.sup.1 是较低的烷氧基，R.sup.2 是溴或较低的烷氧基，R.sup.3 是芳基、杂环芳基或一个基团--Q--R.sup.30，其中 Q 是乙烯基、乙烯基或乙炔基，R.sup.30 是芳基、杂环芳基、较低的烷氧基羰基或氨基甲酰基；公式 I 的羧酸的可水解酯；以及这些化合物的药用可接受的盐，适用于治疗传染病。
• Antiviral Activity of 4-Oxoquinoline-3 - Carboxamide Derivatives against Bovine Herpesvirus Type 5
  作者：Ana Maria V Pinto、José Paulo G Leite、Robson SS Marinho、Luana da SM Forezi、Pedro N Batalha、Fernanda da CS Boechat、Anna C Cunha、David O Silva、Ivson L Gama、Letícia V Faro、Maria CBV de Souza、Izabel Christina P Paixão

  DOI：10.3851/imp3329

  日期：2020.1

  Bovine herpesvirus type 5 is an important agent of meningoencephalitis in cattle and has been identified in outbreaks of bovine neurological disease in several Brazilian states. In recent years, oxoquinoline derivatives have become an important focus in antiviral drug research.

  The cytotoxicity and anti BoHV-5RJ42/01 activity of a set of synthetic 4-oxoquinoline derivatives 4a-k were assayed on Madin–Darby Bovine Kidney cell and antiviral activity by plaque reduction assay. Results: The most promising substance (4h) exhibited CC₅₀and EC₅₀values of 1,239 μM ±5.5 and 6.0 μM ±1.5, respectively, with an SI =206. Two other compounds 4j (CC₅₀= 35 μM ±2 and EC₅₀= 24 μM ±7.0) and 4k (CC₅₀= 55 μM ±2 and EC₅₀= 24 μM ±5.1) presented similar inhibitory profile and selectivity indexes of 1.4 and 2.9, respectively. The results of the time-of-addition studies revealed expressive reduction of virus production (≥80%) in different stages of virus replication cycle except for compound 4h that slightly inhibited virus yield in the first 2 h post infection, but it showed expressive virus inhibition after this time.

  All three compounds slightly interact with the virus on the virucidal assay and they are not able to block virus attachment and penetration. Antiviral effect of oxoquinoline 4h was more prominent than acyclovir which leads us to suggest compound 4h as a promising molecule for further anti-BoHV-5 drug design.

  背景牛疱疹病毒 5 型是牛脑膜脑炎的重要病原体，已在巴西多个州爆发的牛神经系统疾病中被发现。近年来，氧化喹啉衍生物已成为抗病毒药物研究的一个重点。方法在麦丁达比牛肾细胞上检测了一组合成的 4-oxoquinoline 衍生物 4a-k 的细胞毒性和抗 BoHV-5RJ42/01 活性，并通过斑块还原试验检测了其抗病毒活性。结果：最有希望的物质（4h）的 CC50 和 EC50 值分别为 1,239 μM ±5.5 和 6.0 μM ±1.5，SI =206。另外两种化合物 4j（CC50= 35 μM ±2，EC50= 24 μM ±7.0）和 4k（CC50= 55 μM ±2，EC50= 24 μM ±5.1）具有相似的抑制作用，选择性指数分别为 1.4 和 2.9。添加时间的研究结果表明，在病毒复制周期的不同阶段，除了化合物 4h 在感染后的前 2 h 稍微抑制了病毒产量外，其他化合物都明显减少了病毒产量（≥80%）。氧化喹啉 4h 的抗病毒效果比阿昔洛韦更突出，因此我们建议将化合物 4h 作为进一步设计抗 BoHV-5 药物的理想分子。