6-氯-4-羟基-2-(三氟甲基)喹啉 | 18706-21-3

• 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-氯-4-羟基-2-(三氟甲基)喹啉
• 中文别名: 2-三氟甲基-4-羟基-6-氯喹啉；6-氯-4-羟基-2-三氟甲基喹啉
• 英文名称: 6-chloro-2-(trifluoromethyl)quinolin-4-ol
• 英文别名: 6-chloro-2-(trifluoromethyl)-1H-quinolin-4-one
• CAS: 18706-21-3
• 化学式: C₁₀H₅ClF₃NO
• mdl: MFCD12147916
• 分子量: 247.604
• InChiKey: MGEMMMJZAWYWNI-UHFFFAOYSA-N

物化性质

• 熔点：
  280 °C
• 稳定性/保质期：

  常温常压下稳定，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R20/21/22
• 海关编码：
  2933499090
• 危险类别：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  常温下应密闭避光，存放在通风干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
6-Chloro-2-(trifluoromethyl)quinolin-4-ol
Product Name:
Synonyms: 6-Chloro-4-hydroxy-2-(trifluoromethyl)quinoline

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
6-Chloro-2-(trifluoromethyl)quinolin-4-ol
Ingredient name:
CAS number: 18706-21-3

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H5ClF3NO
Molecular weight: 247.6

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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, 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：

  6-氯-4-羟基-2-(三氟甲基)喹啉 在 三氯氧磷 作用下， 反应 2.0h， 以98.88%的产率得到4,6-二氯-2-(三氟甲基)喹啉
  参考文献：
  名称：

  [EN] MODULATORS OF MAS-RELATED G-PROTEIN RECEPTOR X2 AND RELATED PRODUCTS AND THEIR USE
  [FR] MODULATEURS DU RÉCEPTEUR X2 DE LA PROTÉINE G LIÉE AU MAS ET PRODUITS APPARENTÉS ET LEUR UTILISATION

  摘要：

  本发明提供了调节MRGPRX2或MRGPRX2同源物的方法，或更具体地治疗MRGPRX2或MRGPRX2同源物依赖性疾病的方法，通过向需要的受体中注射具有结构（I）的化合物或其药学上可接受的盐、异构体、水合物、溶剂化物或同位素的有效剂量，其中W、Z、R1、R2、R3、R4、R5、R6和Rx的定义如本文所述。本发明还提供了包含这些化合物的制药组合物，以及这些化合物本身。

  公开号：

  WO2022087083A1
• 作为产物：
  描述：

  (Z)-3-(4-Chloro-phenylamino)-4,4,4-trifluoro-but-2-enoic acid ethyl ester 在 PPA 作用下， 反应 2.0h， 以80%的产率得到6-氯-4-羟基-2-(三氟甲基)喹啉
  参考文献：
  名称：

  2-（F-烷基）-4-羟基喹啉的简便合成方法[1]

  摘要：

  已经开发了一种方便的2-（F-烷基）-4-羟基喹啉的新途径。在三乙胺存在下，在70°C的乙腈中用芳香胺处理2,2-二氢多氟链烷酸乙酯，得到相应的烯胺和亚胺的混合物，将其在170°C的多磷酸（PPA）中环化，得到2 -（F-烷基）-4-羟基喹啉具有良好的收率。

  DOI：

  10.1016/s0022-1139(00)83977-9

文献信息

• Design and synthesis of ibuprofen-quinoline conjugates as potential anti-inflammatory and analgesic drug candidates
  作者：Amany M. Ghanim、Adel S. Girgis、Benson M. Kariuki、Nermin Samir、Mona F. Said、Anwar Abdelnaser、Soad Nasr、Mohamed S. Bekheit、Mohamed F. Abdelhameed、Ahmad J. Almalki、Tarek S. Ibrahim、Siva S. Panda

  DOI：10.1016/j.bioorg.2021.105557

  日期：2022.2

  properties in the carrageenan-induced rat paw edema test without showing any ulcerogenic liability. In addition, most conjugates showed promising peripheral analgesic activity in the acetic acid-induced writhing test as well as central analgesic properties in the in vivo hot plate test. The most promising conjugates were the unsubstituted and 6-substituted fluoro- and chloro-derivatives of 2-(trifl

  利用分子杂交方法中的优化反应程序，以良好的收率合成了一组新的布洛芬-喹啉共轭物，包括通过烷基链连接的喹啉基杂环和布洛芬部分，以克服当前非甾体类抗炎药的缺点。筛选合成的缀合物的抗炎和致溃疡特性。在角叉菜胶诱导的大鼠爪水肿试验中发现几种缀合物具有显着的抗炎特性，而没有显示出任何致溃疡的倾向。此外，大多数缀合物在乙酸诱导的扭体试验中显示出有希望的外周镇痛活性以及在体内的中枢镇痛特性热板测试。最有希望的缀合物是通过丙基链与布洛芬连接的 2-(三氟甲基)喹啉的未取代和 6-取代的氟代和氯代衍生物。针对 RAW264.7 小鼠巨噬细胞中 LPS 刺激的炎症反应评估了它们的抗炎活性。在这方面，发现大多数缀合物能够显着减少LPS刺激的巨噬细胞中一氧化氮的释放和产生。促炎细胞因子 IL-6、TNF-α 和诱导型一氧化氮合酶 (iNOS) 的分泌和表达也被显着抑制。
• Quinoline and ferrocene conjugates: Synthesis, computational study and biological evaluations
  作者：Silvija Maračić、Jasmina Lapić、Senka Djaković、Teuta Opačak-Bernardi、Ljubica Glavaš-Obrovac、Valerije Vrček、Silvana Raić-Malić

  DOI：10.1002/aoc.4628

  日期：2019.1

  O‐alkylated quinoline and N‐alkylated 4‐quinolone derivatives attached to the ferrocene moiety through 4,1‐ (7a–d, 8a–d and 12a–d) and 1,4‐disubstituted (9a, 9b, 10a and 10b) 1,2,3‐triazole moiety were synthesized. The observed regioselectivity of O‐ vs. N‐alkylation was explored by the use of NMR and computational techniques. Among the N‐alkylated derivatives, the quinolone‐ferrocene conjugate 9a displayed

  新型O烷基化喹啉和N烷基化4喹诺酮衍生物通过4,1-（7a-d，8a-d和12a-d）和1,4-二取代（9a，9b，10a和10b）连接到二茂铁部分）合成了1,2,3-三唑部分 通过使用NMR和计算技术探索了观察到的O-与N-烷基化的区域选择性。在N烷基化衍生物中，喹诺酮-二茂铁共轭物9a在爆炸危机（K562）和伯基特淋巴瘤（Raji）中显示出显着的抗慢性髓性白血病的活性。6-氯喹诺酮-二茂铁结合物12c对Raji细胞具有选择性抑制活性，对正常MDCK1细胞无抑制作用，被认为是一组O-烷基化喹啉中最有希望的抗癌有机金属复合物。
• Antibacterial activity of new substituted 4-N-alkylated-2-trifluoromethyl-quinoline analogues against sensitive and resistant Mycobacterium tuberculosis strains
  作者：Emerson Teixeira da Silva、Gabriel Fernandes de Andrade、Adriele da Silva Araújo、Maria Cristina Silva Lourenço、Marcus Vinícius Nora de Souza

  DOI：10.1016/j.ejps.2020.105596

  日期：2021.2

  resistant strain has aggravated the tuberculosis situation in the world, running out of control and hard to fight. We evaluate forty new quinoline analogues against sensitive and resistant Mycobacterium tuberculosis (Mtb). Methods; The compounds were obtained via synthesis and evaluated against sensitive strain ATCC 27294. Selected compounds were evaluated against resistant strains SR 2571/0215 and

  目标 抗药性菌株的出现加剧了世界结核病的状况，失去了控制，难以抵抗。我们评估了针对敏感和耐药结核分枝杆菌（Mtb）的40种新喹啉类似物。 方法; 通过合成获得化合物，并针对敏感菌株ATCC 27294进行评估。使用MABA方法，对选定的化合物针对SR 2571/0215和T113 / 09耐药菌株进行评估。选择更具活性的化合物，因为它们对人巨噬细胞具有潜在的细胞毒活性。 结果； 29种化合物对敏感菌株具有活性，而13种对抗性菌株具有活性。针对敏感菌株，最有前途的化合物是4c和4d（MIC分别为9和12μM）。对于抗药性菌株，化合物4a，4d显示出最佳结果（分别为MIC = 4和5μM）。活性化合物4a，4d，6d，7c，8d和10d在接近MIC的浓度下对宿主细胞无细胞毒性。复合的无细胞毒性4d对抗药性和敏感性Mtb最有效。 结论 这些发现有助于寻找敏感和耐药结核病的新生物活性化合物的相关信
• Synthesis of Potential Antiviral Agents for SARS-CoV-2 Using Molecular Hybridization Approach
  作者：Kailey A. Wyman、Adel S. Girgis、Pragnakiran S. Surapaneni、Jade M. Moore、Noura M. Abo Shama、Sara H. Mahmoud、Ahmed Mostafa、Reham F. Barghash、Zou Juan、Radha D. Dobaria、Ahmad J. Almalki、Tarek S. Ibrahim、Siva S. Panda

  DOI：10.3390/molecules27185923

  日期：——

  hybridization approach with good yields. The antiviral properties of the synthesized conjugates against the SAR-CoV-2 virus were investigated and their cytotoxicity was also determined. Among all the synthesized conjugates, compound 9f showed potential against SARS-CoV-2 and low cytotoxicity. The conjugates’ selectivity indexes (SIs) were determined to correlate the antiviral properties and cytotoxicity. The observed

  我们使用分子杂交方法合成了一组具有良好收率的小分子。研究了合成的偶联物对 SAR-CoV-2 病毒的抗病毒特性，并确定了它们的细胞毒性。在所有合成的偶联物中，化合物9f显示出抗 SARS-CoV-2 的潜力和低细胞毒性。结合物的选择性指数 (SI) 被确定为与抗病毒特性和细胞毒性相关。使用计算研究进一步验证了观察到的生物学数据。
• Antitubercular Activity of Novel 2-(Quinoline-4-yloxy)acetamides with Improved Drug-Like Properties
  作者：Ana Flávia Borsoi、Laura Manzoli Alice、Nathalia Sperotto、Alessandro Silva Ramos、Bruno Lopes Abbadi、Fernanda Souza Macchi Hopf、Adilio da Silva Dadda、Raoní S. Rambo、Rodrigo Braccini Madeira Silva、Josiane Delgado Paz、Kenia Pissinate、Mauro Neves Muniz、Christiano Ev Neves、Luiza Galina、Laura Calle González、Marcia Alberton Perelló、Alexia de Matos Czeczot、Mariana Leyser、Sílvia Dias de Oliveira、Graziela de Araújo Lock、Bibiana Verlindo de Araújo、Teresa Dalla Costa、Cristiano Valim Bizarro、Luiz Augusto Basso、Pablo Machado

  DOI：10.1021/acsmedchemlett.2c00254

  日期：2022.8.11

  2-(quinoline-4-yloxy)acetamides was synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (Mtb) growth. Structure–activity relationship studies led to selective and potent antitubercular agents with minimum inhibitory concentrations in the submicromolar range against drug-sensitive and drug-resistant Mtb strains. An evaluation of the activity of the lead compounds against a spontaneous

  利用环烷基和给电子基团降低羰基亲电性，合成了一系列新型 2-(喹啉-4-基氧基)乙酰胺，并对其作为结核分枝杆菌 (Mtb) 生长的体外抑制剂进行了评估。结构-活性关系研究产生了选择性和有效的抗结核药物，其对药物敏感和耐药的结核分枝杆菌菌株的最低抑制浓度在亚微摩尔范围内。对先导化合物针对自发qcrB突变株的活性的评估表明，这些结构靶向细胞色素bc 1复合物。此外，选定的分子在结核感染的巨噬细胞模型中抑制结核分枝杆菌的生长。此外，根据具体情况，先导化合物具有化学稳定性，并表现出良好的动力学溶解度、高渗透性和低体外代谢率。最后，在小鼠口服给药后评估该化合物的药代动力学特征。据我们所知，首次在充分暴露的情况下获得了2-(喹啉-4-基氧基)乙酰胺，这可能使其具有体内有效性并进一步开发为抗结核候选药物。