6-溴-4-羟基-3-喹啉羧酸乙酯 | 122794-99-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 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-4-羟基-3-喹啉羧酸乙酯
• 中文别名: 4-羟基-6-溴喹啉-3-羧酸乙酯；6 -溴- 4 -羟基- 3 -喹啉羧酸乙酯
• 英文名称: ethyl 6-bromo-4-hydroxyquinoline-3-carboxylate
• CAS: 122794-99-4
• 化学式: C₁₂H₁₀BrNO₃
• mdl: MFCD01911606
• 分子量: 296.12
• InChiKey: IVZIOBTVAJBBAS-UHFFFAOYSA-N

物化性质

• 熔点：
  326-329°C
• 沸点：
  385.5±37.0 °C(Predicted)
• 密度：
  1.593

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

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36
• WGK Germany：
  3
• 海关编码：
  2933499090
• 危险类别：
  IRRITANT
• 危险标志：
  GHS07
• 危险性描述：
  H319
• 危险性防范说明：
  P305 + P351 + P338
• 储存条件：
  室温下，应保存在惰性气体中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 6-bromo-4-hydroxyquinoline-3-carboxylate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H319: Causes serious eye irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

---

Section 3. Composition/information on ingredients.
Ingredient name: Ethyl 6-bromo-4-hydroxyquinoline-3-carboxylate
CAS number: 122794-99-4

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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.
Storage: Store in closed vessels.

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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: 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.

---

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

制备方法与用途

概述

6-溴-4-羟基-3-喹啉羧酸乙酯可用作医药化工合成中间体，在农药、医药和有机合成等领域有着较为广泛的应用。

应急措施

若吸入6-溴-4-羟基-3-喹啉羧酸乙酯，请立即将患者移至空气新鲜处；如皮肤接触，应脱去污染衣物，并用肥皂水及清水彻底清洗；如有不适，请及时就医。如眼睛接触到该物质，请分开眼睑，用流动清水或生理盐水冲洗，并立即寻求医疗帮助。若误食，请即刻漱口，禁止催吐，并尽快就医。

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 6-bromo-4-methoxyquinoline-3-carboxylate	1841096-87-4	C12H10BrNO3	296.12
  6-溴-4-氯-3-喹啉羧酸乙酯	ethyl 6-bromo-4-chloroquinoline-3-carboxylate	206257-39-8	C12H9BrClNO2	314.566
  6-溴-4-氧代-1,4-二氢喹啉-3-羧酸	6-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid	302553-00-0	C10H6BrNO3	268.067
  ——	ethyl 4-chloro-6-ethenyl-3-quinolinecarboxylate	916812-34-5	C14H12ClNO2	261.708
  ——	ethyl 6-bromo-4-(3-morpholinopropylamino)quinoline-3-carboxylate	——	C19H24BrN3O3	422.322
  ——	ethyl 6-bromo-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylate	179942-70-2	C14H14BrNO3	324.174
  ——	ethyl 6-bromo-4-((3-(trifluoromethyl)phenyl)amino)quinoline-3-carboxylate	449197-54-0	C19H14BrF3N2O2	439.232
  ——	ethyl 6-bromo-4-(4-morpholinyl)-3-quinolinecarboxylate	916812-69-6	C16H17BrN2O3	365.227
  ——	ethyl 6-bromo-4-((3-nitrophenyl)amino)quinoline-3-carboxylate	——	C18H14BrN3O4	416.231
  ——	ethyl 4-((3-(1H-imidazol-1-yl)propyl)amino)-6-bromoquinoline-3-carboxylate	1356941-10-0	C18H19BrN4O2	403.278

反应信息

• 作为反应物：
  描述：

  6-溴-4-羟基-3-喹啉羧酸乙酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基溴化铵 、 tri tert-butylphosphoniumtetrafluoroborate potassium fluoride 、 叠氮磷酸二苯酯 、 水 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 1,3-二氢-8-[5-(1-羟基-1-甲基乙基)-3-吡啶基]-1-[(2S)-2-甲氧基丙基]-3-甲基-2H-咪唑并[4,5-c]喹啉-2-酮
  参考文献：
  名称：

  PI3 KINASE/mTOR DUAL INHIBITOR

  摘要：

  本发明提供了一种imidazo[4,5-c]quinolin-2-one化合物，或其药用可接受的盐，可以抑制PI3K和mTOR，因此在癌症治疗中具有用处。

  公开号：

  US20120184577A1
• 作为产物：
  描述：

  (4-溴苯胺亚甲基)丙二酸二乙酯 以 二苯醚 为溶剂， 反应 1.0h， 以61%的产率得到6-溴-4-羟基-3-喹啉羧酸乙酯
  参考文献：
  名称：

  吲哚[3,2-c]喹啉G-四链体稳定剂：与人类端粒G-四链体结合的结构分析

  摘要：

  评估了具有烷基二胺侧链各种取代模式的5-甲基吲哚并[3,2- c ]喹诺酮（IQc）库的G-四链体（G4）结合方式和效率。荧光共振能量转移解链分析表明，杂芳族核中带有正电荷的IQcs和两个弱碱性侧链是有效的和选择性的人类端粒（HT）和基因启动子G4稳定剂。以HT G4为模型的光谱研究表明，IQc稳定复合物涉及两个IQc分子（2,9-双{[3-（二乙基氨基）丙基]氨基} -5-甲基-11 H-吲哚[3， 2 c ]喹啉5氯化铵，3 d）每个G4单位，位于两个非独立但等效的结合位点。分子动力学研究表明，3 d的末端堆积诱导了G4结构的构象重排，从而驱动了第二个3 d配体与G4凹槽的结合。建模研究还表明，具有两个三碳侧链的3 d具有合适的几何形状，可通过侧链的末端氮原子参与直接或水介导的氢键结合到磷酸盐骨架和/或G4环上。此外，抗增殖研究表明IQc化合物2 d（2-{{[3-（二乙基氨基）丙基]氨基}

  DOI：

  10.1002/cmdc.201500067

文献信息

• [EN] COMBINATION OF KINASE INHIBITORS AND USES THEREOF<br/>[FR] COMBINAISON D'INHIBITEURS DE KINASE ET SES UTILISATIONS
  申请人：INTELLIKINE LLC

  公开号：WO2014151147A1

  公开（公告）日：2014-09-25

  The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In yet another aspect, a method of inhibiting phosphorylation of both Akt (S473) and Akt (T308) in a cell is set forth. The present invention also provides a pharmaceutical kit effective for treating a disease condition associated with PI3 -kinase α and/or mTOR in a subject.

  本发明提供了一种治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的方法。另一方面，该发明提供了一种治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的方法。在另一个方面，提出了一种抑制细胞内Akt（S473）和Akt（T308）磷酸化的方法。本发明还提供了一种有效治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的药物套装。
• COMBINATION OF KINASE INHIBITORS AND USES THEREOF
  申请人：INTELLIKINE, LLC

  公开号：US20150030588A1

  公开（公告）日：2015-01-29

  The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or a receptor tyrosine kinase (RTK) in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase α and/or an RTK in a subject. In yet another aspect, a method of inhibiting phosphorylation of Akt (S473) in a cell is set forth.

  本发明提供了一种治疗与PI3-激酶a和/或受体酪氨酸激酶（RTK）有关的疾病状况的方法。另一方面，该发明提供了一种治疗与PI3-激酶α和/或受体酪氨酸激酶（RTK）有关的疾病状况的方法。另一方面，提出了一种抑制细胞中Akt（S473）磷酸化的方法。
• [EN] AGENTS FOR USE IN THE TREATMENT OF CARDIOVASCULAR AND INFLAMMATORY DISEASES STRUCTURALLY BASED ON 4(1 H)-QUINOLONE<br/>[FR] AGENTS DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE MALADIES CARDIOVASCULAIRES ET INFLAMMATOIRES AYANT UNE STRUCTURE BASÉE SUR LA 4(1H)-QUINOLONE
  申请人：UCL BUSINESS PLC

  公开号：WO2015189560A1

  公开（公告）日：2015-12-17

  The present invention provides a compound of formula I, a tautomer thereof, or a pharmaceutically acceptable salt or N-oxide thereof for use in the treatment or prevention of a cardiovascular disease or of an inflammatory disease or condition:

  本发明提供了一种式I的化合物，其互变异构体，或其药用可接受的盐或N-氧化物，用于治疗或预防心血管疾病或炎症性疾病或症状。
• [EN] PAPD5 INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE PAPD5 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CHILDRENS MEDICAL CENTER

  公开号：WO2020219729A1

  公开（公告）日：2020-10-29

  The present application provides compounds that are PAPD5 inhibitors and are useful in treating a variety of conditions such as cancer, telomere diseases, and aging-related and other degenerative disorders.

  本申请提供了一些PAPD5抑制剂化合物，可用于治疗各种疾病，如癌症、端粒疾病以及与衰老和其他退行性疾病相关的情况。
• Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof
  申请人：Ren Pingda

  公开号：US09295673B2

  公开（公告）日：2016-03-29

  The present invention provides for a method for treating a disease condition associated with PI3-kinase α and/or mTOR in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase α and/or mTOR in a subject. In yet another aspect, a method of inhibiting phosphorylation of both Akt (S473) and Akt (T308) in a cell is set forth.

  本发明提供了一种治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的方法。另一方面，该发明提供了一种治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的方法。在另一个方面，提出了一种抑制细胞内Akt（S473）和Akt（T308）的磷酸化的方法。