4-羟基-8-三氟甲基喹啉-3-甲酸乙酯 | 23851-84-5

• 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: 4-羟基-8-三氟甲基喹啉-3-甲酸乙酯
• 中文别名: 4-羟基-8-三氟甲基喹啉-3-羧酸乙酯
• 英文名称: 4-hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 4-hydroxy-8-(trifluoromethyl)quinoline-3-carboxylate；ethyl 8-(trifluoromethyl)-4-hydroxyquinoline-3-carboxylate；ethyl 4-hydroxy-8-trifluoromethylquinoline-3-carboxylate；4-Hydroxy-8-(trifluoromethyl)-3-quinolinecarboxylic acid ethyl ester；3-Carbethoxy-4-hydroxy-8-trifluormethyl-chinolin；ethyl 4-oxo-8-(trifluoromethyl)-1H-quinoline-3-carboxylate
• CAS: 23851-84-5
• 化学式: C₁₃H₁₀F₃NO₃
• mdl: MFCD00173387
• 分子量: 285.223
• InChiKey: XSNJFNKOHAUNPO-UHFFFAOYSA-N

物化性质

• 熔点：
  216 °C(Solv: ethanol (64-17-5))
• 沸点：
  343.5±37.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xi
• 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 4-hydroxy-8-trifluoromethylquinoline-3-carboxylate
Synonyms: Ethyl 4-oxo-8-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

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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 4-hydroxy-8-trifluoromethylquinoline-3-carboxylate
CAS number: 23851-84-5

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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: C13H10F3NO3
Molecular weight: 285.2

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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 fluoride.

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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-羟基-8-三氟甲基喹啉-3-甲酸乙酯 在 三氯氧磷 作用下， 生成 4-氯-8-三氟甲基喹啉-3-羧酸乙酯
  参考文献：
  名称：

  喹啉-3-甲酰胺，含砜作为肝X受体（LXR）激动剂，对LXRβ具有结合选择性，且血脑渗透率低

  摘要：

  制备了一系列包含喹啉-3-甲酰胺的砜，发现它们具有对LXRβ的良好结合亲和力和对LXRα的中等结合选择性。TPSA得分高的8-Cl喹啉类似物33对LXRβ的结合选择性超过LXRα的34倍（LXRβIC 50  = 16 nM），在THP巨噬细胞系中诱导ABCA1基因表达的活性良好，所需的弱效LXRαGal4功能测定和低血脑屏障穿透力在大鼠中。

  DOI：

  10.1016/j.bmcl.2009.11.062
• 作为产物：
  描述：

  2-((2-三氟甲基苯基氨基)亚甲基)丙二酸二乙酯 在 Dowtherm 作用下， 反应 5.0h， 以94.1%的产率得到4-羟基-8-三氟甲基喹啉-3-甲酸乙酯
  参考文献：
  名称：

  点击化学方法：区域选择性的一锅合成一些新的基于8-三氟甲基喹啉的1,2,3-三唑类作为有效的抗菌剂

  摘要：

  通过点击化学方法，通过多步反应合成了三组基于8-三氟甲基喹啉的1,2,3-三唑衍生物（5a – c，6a – d和7a – c）。合成的化合物通过光谱研究和X射线分析进行表征。通过孔板法（抑制区）筛选最终化合物的体外抗菌活性。发现化合物5c，6b，8b，11和12对测试的微生物菌株具有活性。结果总结在表5和6中。

  DOI：

  10.1016/j.ejmech.2014.01.008

文献信息

• Quinolines useful in treating cardiovascular disease
  申请人：Collini D. Michael

  公开号：US20050131014A1

  公开（公告）日：2005-06-16

  This invention provides compounds of formula I that are useful in the treatment or inhibition of LXR mediated diseases.

  本发明提供了式I化合物的用途，它们在治疗或抑制LXR介导的疾病中是有用的。
• Unsymmetrical Bisquinolines with High Potency against P. falciparum Malaria
  作者：Katherine M. Liebman、Steven J. Burgess、Bornface Gunsaru、Jane X. Kelly、Yuexin Li、Westin Morrill、Michael C. Liebman、David H. Peyton

  DOI：10.3390/molecules25092251

  日期：——

  Quinoline-based scaffolds have been the mainstay of antimalarial drugs, including many artemisinin combination therapies (ACTs), over the history of modern drug development. Although much progress has been made in the search for novel antimalarial scaffolds, it may be that quinolines will remain useful, especially if very potent compounds from this class are discovered. We report here the results of

  在现代药物开发的历史中，基于喹啉的支架一直是抗疟药物的中流砥柱，包括许多青蒿素联合疗法 (ACTs)。尽管在寻找新型抗疟支架方面取得了很大进展，但喹啉可能仍然有用，特别是如果发现了此类非常有效的化合物。我们在此报告了结构-活性关系 (SAR) 研究的结果，该研究评估了潜在的不对称双喹啉抗疟原虫药物候选物，该研究使用针对细胞培养中完整寄生虫的体外活性。发现许多不对称双喹啉对氯喹敏感和对氯喹具有抗性的恶性疟原虫寄生虫均具有高度效力。
• Quinoline derivatives and medicinal use thereof
  申请人：——

  公开号：US20030212100A1

  公开（公告）日：2003-11-13

  A quinoline derivative represented by the following formula (1): 1 allows PPAR&agr; or &ggr; which is an intranuclear transcription factor, to function strongly and is low in toxicity. By using this compound as an active ingredient, there can be provided a preventive or therapeutic agent for various diseases related to PPAR&agr; or &ggr;.

  由以下式（1）表示的喹啉衍生物，可以使作为细胞核转录因子的PPAR&agr;或&ggr;功能强大且毒性低。通过使用这种化合物作为活性成分，可以提供与PPAR&agr;或&ggr;相关的各种疾病的预防或治疗剂。
• Quinolines and pharmaceutical compositions thereof
  申请人：Wyeth

  公开号：US07576215B2

  公开（公告）日：2009-08-18

  This invention provides compounds of formula I that are useful in the treatment or inhibition of LXR mediated diseases.

  本发明提供了I式化合物，可用于治疗或抑制LXR介导的疾病。
• Design, semi-synthesis and molecular docking of new antibacterial and antibiofilm triazole conjugates from hydroxy-triterpene acids and fluoroquinolones
  作者：Besma Boulila、Mabrouk Horchani、Raphael Duval、Mohamed Othman、Adam Daïch、Hichem Ben Jannet、Anis Romdhane、Ata Martin Lawson

  DOI：10.1039/d3nj02922k

  日期：——

  from isolated pentacyclic triterpene acids as natural products from olive pomace (Olea europaea L.). These conjugates were synthesized via a last step of Cu-catalyzed azide–alkyne cycloaddition (CuAAC) between propargylated quinolone/fluoroquinolones (QN/FQNs) and MA/OA azides to achieve new triazole derivatives in overall excellent yields. The latter hybrids were screened in vitro for their antibacterial

  以橄榄果渣 ( Olea europaea L.) 的天然产物分离五环三萜酸为原料，设计并半合成了一系列具有有效抗菌和抗生物膜活性的山楂酸 (MA) 和齐墩果酸 (OA) 类似物。这些缀合物是通过铜催化的叠氮化物-炔环加成 (CuAAC) 的最后一步合成的，在炔丙基化喹诺酮/氟喹诺酮 (QN/FQNs) 和 MA/OA 叠氮化物之间进行，以总体优异的收率获得新的三唑衍生物。后者的杂交体在体外筛选其对两种革兰氏阳性菌（金黄色葡萄球菌和粪肠球菌）和两种革兰氏阴性菌（金黄色葡萄球菌和粪肠球菌）的抗菌和抗生物膜活性。大肠杆菌和铜绿假单胞菌）。结果表明，一些山楂酸衍生物对所有测试菌株均表现出显着的活性，其 MIC 值在 3.25–30 μg mL -1范围内。此外，评估的化合物具有中度至显着的抗生物膜活性，对金黄色葡萄球菌生物膜形成的抑制百分比高达 68.75% 。使用合成化合物抗菌活性对接研究的分