4-羟基-8-甲基喹啉-3-羧酸乙酯 | 77156-75-3

• 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-甲基喹啉-3-羧酸乙酯
• 中文别名: 4-羟基-8-甲基喹啉-3-甲酸乙酯；8-甲基-4-氧代-1,4-二氢喹啉-3-羧酸乙酯乙酯
• 英文名称: 4-hydroxy-8-methyl-quinoline-3-carboxylic acid ethyl ester
• 英文别名: 4-Hydroxy-8-methyl-chinolin-3-carbonsaeure-aethylester；ethyl 4-hydroxy-8-methylquinoline-3-carboxylate
• CAS: 77156-75-3
• 化学式: C₁₃H₁₃NO₃
• mdl: MFCD01847815
• 分子量: 231.251
• InChiKey: HYUYDOCMASKUMM-UHFFFAOYSA-N

物化性质

• 熔点：
  271-274°(dec)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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
• 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
• 储存条件：
  室温下，应保存于惰性气体中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 4-hydroxy-8-methylquinoline-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 4-hydroxy-8-methylquinoline-3-carboxylate
CAS number: 77156-75-3

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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, refrigerated.

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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: C13H13NO3
Molecular weight: 231.2

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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.

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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-甲基喹啉-3-羧酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 以91%的产率得到4-hydroxy-8-methylquinoline-3-hydrazide
  参考文献：
  名称：

  合成的4-Oxo-1,4-二氢喹啉新的1,3,4-氧杂二唑，噻二唑，1,2,4-三唑和丁二酰肼衍生物的抗菌评价

  摘要：

  一系列取代的1,3,4-恶二唑，1,2,4-三唑和1,3,4-噻二唑衍生物 通过关键中间体硫代氨基脲衍生物与不同试剂的反应合成了3-carboethoxy-1,4-dihydro-4-oxoquinoline。N'-亚芳基-4-氧代-1,4-二氢喹啉-3-碳酰肼也通过相应的酰肼与适当的醛的缩合反应合成。评价了一些合成化合物的抗菌活性。

  DOI：

  10.1002/jhet.1005
• 作为产物：
  描述：

  邻甲苯胺 在 2-氯苯甲酸 作用下， 反应 3.0h， 生成 4-羟基-8-甲基喹啉-3-羧酸乙酯
  参考文献：
  名称：

  新型喹诺酮-3-羧酸衍生物作为抗HIV-1药物：设计，合成和生物活性

  摘要：

  合成了一系列新的喹诺酮-3-羧酸，它们在N-1，C-2，C-7和C-8位置具有不同的疏水基团，并评估了它们对单周期可复制HIV NL4-3的抑制作用Hela细胞培养物中p 24的表达速率。大多数合成的化合物在100μM的浓度下均具有抗HIV活性，且无明显的细胞毒性。活性最高的化合物4h，4k和4j表现出抗HIV活性，抑制率分别为55％，71％和84％。使用可用于PFV整合酶的晶体学数据（包括其与Mg 2+的配合物）进行的对接研究Raltegravir和Raltegravir揭示，活性化合物可以在Raltegravir附近占据相同的空间，并与活性位点中的Mg 2 +离子相互作用。因此，合成化合物的抗HIV活性可能涉及金属螯合机制。

  DOI：

  10.1007/s00044-016-1631-x

文献信息

• 3-(Benzo[<i>d</i>]thiazol-2-yl)-4-aminoquinoline derivatives as novel scaffold topoisomerase I inhibitor <i>via</i> DNA intercalation: design, synthesis, and antitumor activities
  作者：Jing-Mei Yuan、Nan-Ying Chen、Hao-Ran Liao、Guo-Hai Zhang、Xiao-Juan Li、Zi-Yu Gu、Cheng-Xue Pan、Dong-Liang Mo、Gui-Fa Su

  DOI：10.1039/c9nj05846j

  日期：——

  Twenty-seven 3-(benzo[d]thiazol-2-yl)-4-aminoquinoline derivatives have been designed and synthesized as topoisomerase I inhibitors. The in vitro anti-proliferation evaluation against four human cancer cell lines (MGC-803, HepG-2, T24, and NCI-H460) and one normal cell line (HL-7702) indicated that most of them exhibited potent cytotoxicity. Among them, 5a was identified as the most promising candidate

  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
• Synthesis of 6-aryl substituted 4-quinolones via Suzuki cross coupling
  作者：Sumanta Gupta、Prasanjit Ghosh、Seema Dwivedi、Sajal Das

  DOI：10.1039/c3ra45056b

  日期：——

  A convenient way to introduce aryl functionalization in the 6-position of 4-quinolones is developed via selective bromination and subsequent arylation by Suzuki cross-coupling. Ethyl 4-quinolone 3-carboxylates were subjected to selective bromination at C-6 followed by arylation under microwave irradiation that yielded the desired cross-coupling products within 5 minutes. This approach can expediently

  通过选择性溴化和随后通过铃木交叉偶联的芳基化作用，开发了一种在4-喹诺酮的6-位引入芳基官能化的简便方法。使4-喹诺酮3-羧酸乙酯在C-6处选择性溴化，然后在微波辐射下进行芳基化，在5分钟内产生所需的交叉偶联产物。该方法可方便地用于芳基官能化的4-喹诺酮衍生物（一类重要的生物活性化合物）的文库合成。
• Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat–TAR interaction inhibitors
  作者：Shuguang Chen、Ran Chen、Meizi He、Ruifang Pang、Zhiwu Tan、Ming Yang

  DOI：10.1016/j.bmc.2009.01.038

  日期：2009.3

  Thirty-two quinoline derivatives were designed and synthesized as HIV-1 Tat–TAR interaction inhibitors. All the compounds showed high antiviral activities in inhibiting the formation of SIV-induced syncytium in CEM174 cells. Nine of them with low cytotoxicities were evaluated by Tat dependent HIV-1 LTR-driven CAT gene expression colorimetric enzyme assay in human 293T cells, indicating effective inhibitory

  设计并合成了32种喹啉衍生物作为HIV-1 TAt-TAR相互作用抑制剂。所有这些化合物在抑制CEM174细胞中SIV诱导的合胞体形成方面均表现出很高的抗病毒活性。在人的293T细胞中，通过TAt依赖HIV-1 LTR驱动的CAT基因表达比色酶分析评估了其中9种低细胞毒性，表明它们具有有效的抑制TAt-TAR相互作用的抑制活性。分子模拟实验表明，这些化合物可能通过与TAt蛋白而非TAR RNA结合而抑制TAt-TAR相互作用。
• 3-(2-苯并五元杂环)-4-(3-二甲胺丙氨基)喹啉衍生物及其制备方法和应用
  申请人：广西师范大学

  公开号：CN109651355A

  公开（公告）日：2019-04-19

  本发明提供一类3‑(2‑苯并五元杂环)‑4‑(3‑二甲胺丙氨基)喹啉衍生物及其制备方法和应用，3‑(2‑苯并五元杂环)‑4‑(3‑二甲胺丙氨基)喹啉衍生物的通式为：。该类化合物具有很好的抗肿瘤活性，能应用于制备抗肿瘤药物。
• Design, Synthesis, Molecular Docking Analysis and Biological Evaluations of 4-[(Quinolin-4-yl)amino]benzamide Derivatives as Novel Anti-Influenza Virus Agents
  作者：Chao Zhang、Yun-Sang Tang、Chu-Ren Meng、Jing Xu、De-Liang Zhang、Jian Wang、Er-Fang Huang、Pang-Chui Shaw、Chun Hu

  DOI：10.3390/ijms23116307

  日期：——

  4-[(quinolin-4-yl)amino]benzamide derivatives as the novel anti-influenza agents were designed and synthesized. Cytotoxicity assay, cytopathic effect assay and plaque inhibition assay were performed to evaluate the anti-influenza virus A/WSN/33 (H1N1) activity of the target compounds. The target compound G07 demonstrated significant anti-influenza virus A/WSN/33 (H1N1) activity both in cytopathic effect assay

  本研究设计合成了一系列4-[(quinolin-4-yl)amino]苯甲酰胺衍生物作为新型抗流感药物。进行细胞毒性试验、细胞病变效应试验和噬斑抑制试验以评估目标化合物的抗流感病毒 A/WSN/33 (H1N1) 活性。目标化合物G07在细胞病变效应试验 (EC 50 = 11.38 ± 1.89 µM) 和噬菌斑抑制试验 (IC 50 = 0.23 ± 0.15 µM)中均表现出显着的抗流感病毒 A/WSN/33 (H1N1) 活性。G07对其他三种不同的流感病毒株 A/PR/8 (H1N1)、A/HK/68 (H3N2) 和乙型流感病毒也表现出显着的抗流感病毒活性。根据核糖核蛋白重组试验结果，G07与核糖核蛋白相互作用良好，在100 µM时抑制率为80.65%。此外，根据最佳药效团 Hypo1 预测的 PA-PB1 抑制活性， G07表现出显着的活性靶标 RNA 聚合酶 PA-PB1