3-氧代-3,4-二氢-2-喹喔啉甲酸乙酯 | 36818-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-氧代-3,4-二氢-2-喹喔啉甲酸乙酯
• 中文别名: 3-氧代-3,4-二氢-2-喹噁啉羧酸乙酯
• 英文名称: ethyl 3-oxo-4H-quinoxaline-2-carboxylate
• 英文别名: ethyl 3-oxo-3,4-dihydroquinoxaline-2-carboxylate；ethyl (quinoxalin-2(1H)-one)-3-carboxylate；3,4-Dihydro-3-oxo-2-quinoxalinecarboxylic acid,ethyl ester
• CAS: 36818-07-2
• 化学式: C₁₁H₁₀N₂O₃
• mdl: MFCD00459589
• 分子量: 218.212
• InChiKey: MIIFHRBUBUHJMC-UHFFFAOYSA-N

物化性质

• 熔点：
  175.5-176.5 °C
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 3-oxo-3,4-dihydro-2-quinoxalinecarboxylate
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 3-oxo-3,4-dihydro-2-quinoxalinecarboxylate
CAS number: 36818-07-2

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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: C11H10N2O3
Molecular weight: 218.2

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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：

  3-氧代-3,4-二氢-2-喹喔啉甲酸乙酯 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 3-carboazide-quinoxalin-2(1H)-one
  参考文献：
  名称：

  Badr, M. Z. A.; Mahgoub, S. A.; Atta, F. M., Journal of the Indian Chemical Society, 1994, vol. 71, # 10, p. 617 - 620

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯喹喔啉-2-甲酸乙酯 在 双氧水 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 70.0h， 生成 3-氧代-3,4-二氢-2-喹喔啉甲酸乙酯
  参考文献：
  名称：

  2-（喹喔啉-2-基氨基氨基苯并三唑基）戊二烯衍生物的合成作为潜在的抗叶酸剂

  摘要：

  抗叶酸剂对癌症，细菌和寄生虫感染（尤其是疟疾）等疾病的治疗计划产生重大影响。喹喔啉衍生物在体外显示具有抗癌活性，并能同时抑制二氢叶酸还原酶和胸苷酸合酶。在这里，我们决定将喹喔啉和喹喔啉1,4-二氧化物的化学性质与苯并三唑核的化学性质结合起来，以评估由此产生的生物学性质。制备了两个主要的新系列，包括60多种化合物。在第一个中，苯并三唑部分通过氮原子1、2或3连接到戊二酸取代基上，以模拟谷氨酸部分。在第二系列中，戊二酸被乙酸部分取代，以评估空间位阻的影响。在这里，我们描述了从市售二胺开始获得所有标题喹喔啉的多步化学过程。所选喹喔啉的经典氧化不成功，

  DOI：

  10.1002/jhet.2474

文献信息

• Amine compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06329389B1

  公开（公告）日：2001-12-11

  The present invention provides a compound of the formula: wherein Ar represents an aromatic group which may be substituted; X represents methylene, S, SO, SO2 or CO; Y represents a spacer having a main chain of 2 to 5 atoms; n represents an integer of 1 to 5; i) R1 and R2 each represents a hydrogen atom or a lower alkyl which may be substituted, ii) R1 and R2 form, taken together with the adjacent nitrogen atom, a nitrogen-containing heterocyclic ring which may be substituted, or iii) R1 or R2 together with —(CH2)n—N═ form, bonded to a component atom of Ring B, a spiro-ring which may be substituted; Ring A represents an aromatic ring which may be substituted; Ring B represents a 4- to 7-membered nitrogen-containing non-aromatic ring which may be further substituted by alkyl or acyl, with a proviso that X represents S, SO, SO2 or CO when Ring A has as a substituent a group represented by the formula: —NHCOR11 where R11 represents alkyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or a group represented by the formula: —NHR12 where R12 represents alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, or a salt thereof; which has an excellent somatostatin receptor binding inhibition action.

  本发明提供了一种化合物，其化学式如下： 其中Ar代表可能被取代的芳香基团； X代表亚甲基、S、SO、SO2或CO； Y代表具有2到5个原子的主链的间隔物； n代表1到5的整数； i）R1和R2分别代表氢原子或可能被取代的较低烷基， ii）R1和R2与相邻的氮原子一起形成可能被取代的含氮杂环环，或 iii）R1或R2与—(CH2)n—N═一起形成，与环B的一个组分原子结合，可能被取代的螺环； 环A代表可能被取代的芳香环； 环B代表可能被烷基或酰基进一步取代的4到7成员的含氮非芳香环， 但有一个条件是，当环A具有由下式表示的基团作为取代基时： —NHCOR11 其中R11代表烷基、烷氧基烷基、烷硫基烷基、环烷基、环烷基烷基、芳基、芳基烷基或由下式表示的基团： —NHR12 其中R12代表烷基、环烷基、环烷基烷基、芳基或芳基烷基，或其盐；具有优异的生长抑素受体结合抑制作用。
• 1,2-Dihydro-2-oxoquinoline derivatives
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：US06329525B1

  公开（公告）日：2001-12-11

  A 1,2-dihydro-2-oxoquinoline derivative represented by the formula: wherein Ar is a pyridyl group or a group represented by the formula: (wherein X3 and X4 are the same or different, and are each a hydrogen atom, a halogen atom, a C1-5 alkyl group, a C1-5 alkoxy group, a hydroxyl group or a trifluoromethyl group), Y is a nitrogen atom, CH or C(OH), R1 and R2 are the same or different, and are each a hydrogen atom, a C1-10 alkyl group, a C3-15 alkoxyalkyl group or a C3-15 alkylaminoalkyl group, or R1 and R2 taken together with the nitrogen atom to which they are attached form a cyclic amino group, X1 and X2 are the same or different, and are each a hydrogen atom, a C1-5 alkyl group, a C1-5 alkoxy group or a halogen atom, or X1 and X2 taken together form an alkylenedioxy group, and n is an integer of 1 to 3; or a pharmaceutically acceptable salt thereof.

  一种由以下公式表示的1,2-二氢-2-氧喹啉衍生物： 其中Ar是吡啶基或由以下公式表示的基团： （其中X3和X4相同或不同，分别为氢原子、卤素原子、C1-5烷基、C1-5烷氧基、羟基或三氟甲基基团），Y是氮原子、CH或C(OH)，R1和R2相同或不同，分别为氢原子、C1-10烷基、C3-15烷氧基烷基或C3-15烷基氨基烷基，或R1和R2与它们连接的氮原子一起形成环状氨基团，X1和X2相同或不同，分别为氢原子、C1-5烷基、C1-5烷氧基或卤素原子，或X1和X2一起形成烷二氧基基团，n为1到3的整数；或其药学上可接受的盐。
• A SAR Study of Novel Antiproliferative Ruthenium and Osmium Complexes with Quinoxalinone Ligands in Human Cancer Cell Lines
  作者：Werner Ginzinger、Gerhard Mühlgassner、Vladimir B. Arion、Michael A. Jakupec、Alexander Roller、Mathea Sophia Galanski、Michael Reithofer、Walter Berger、Bernhard K. Keppler

  DOI：10.1021/jm3000906

  日期：2012.4.12

  yielding IC50 values of 6–60 μM for three unsubstituted metal-free ligands, whereas values for the metal complexes vary in a broad range from 0.3 to 140 μM. Complexation with osmium of quinoxalinone derivatives with benzimidazole or benzothiazole results in a more consistent increase in cytotoxicity than complexation with ruthenium. For selected compounds, the capacity to induce apoptosis was confirmed

  已合成了一系列具有 3-(1 H-苯并咪唑-2-基)-1 H-喹喔啉-2-one 的钌 (II) 芳烃配合物，具有已知蛋白激酶抑制剂的药效基团，以及相关的苯并恶唑和苯并噻唑衍生物. 此外，还制备了相应的未取代配体的锇配合物。这些化合物已通过 NMR、UV-vis 和 IR 光谱、ESI 质谱、元素分析和 X 射线晶体学进行了表征。通过 MTT 测定法测定三种人类癌细胞系（A549、CH1、SW480）的抗增殖活性，产生 IC 50三个未取代的无金属配体的值为 6-60 μM，而金属配合物的值在 0.3 至 140 μM 的宽范围内变化。与苯并咪唑或苯并噻唑与喹喔啉酮衍生物的锇络合导致比与钌络合更一致地增加细胞毒性。对于选定的化合物，通过荧光显微镜和流式细胞术分析证实了诱导细胞凋亡的能力，而细胞周期效应只是中等的。
• New efficient access to fused (Het)Aryltetrahydroindolizinones via N-acyl iminium intermediates
  作者：Matteo Chiurato、Rajaa Boulahjar、Sylvain Routier、Yves Troin、Gérald Guillaumet

  DOI：10.1016/j.tet.2010.03.100

  日期：2010.6

  In this paper, we described the preparation of fused (Het)Aryltetrahydroindolizinones via N-acyl iminium intermediates. Two different routes were also explored to achieve the synthesis. The first one consists in the intramolecular reaction of β-hydroxylactams whereas the second route one is an intermolecular condensation between a 2-formylester or a β-alkoxylactone and an appropriate primary amine

  在本文中，我们描述了通过N-酰基亚胺鎓中间体制备稠合的（Het）芳基四氢吲哚并酮。还探索了两种不同的途径来实现合成。第一种途径是β-羟基内酰胺的分子内反应，而第二种途径是2-甲酸酯或β-烷氧基内酯与适当的伯胺之间的分子间缩合。我们还开发了两种杂环策略来获得吡啶，吡嗪，喹啉和喹喔啉系列中足够的不可用原料，然后进行所有分子间或分子内反应。给出了范围和限制。
• Identification of 3-(benzazol-2-yl)quinoxaline derivatives as potent anticancer compounds: Privileged structure-based design, synthesis, and bioactive evaluation in vitro and in vivo
  作者：Qing-Qing Liu、Ke Lu、Hai-Miao Zhu、Shi-Lin Kong、Jing-Mei Yuan、Guo-Hai Zhang、Nan-Ying Chen、Chen-Xi Gu、Cheng-Xue Pan、Dong-Liang Mo、Gui-Fa Su

  DOI：10.1016/j.ejmech.2019.01.004

  日期：2019.3

  structural characteristics of numerous known antitumor compounds targeting DNA or topoisomerase I, 3-(benzazol-2-yl)-quinoxaline-based scaffold was designed via the combination of two important privileged structure units —quinoxaline and benzazole. Thirty novel 3-(benzazol-2-yl)-quinoxaline derivatives were synthesized and evaluated for their biological activities. The MTT assay indicated that most

  受许多已知的靶向DNA或拓扑异构酶I的抗​​肿瘤化合物的共同结构特征的启发，通过结合两个重要的特权结构单元-喹喔啉和苯并唑，设计了基于3-（苯甲唑-2-基）-喹喔啉的骨架。合成了三十种新颖的3-（苯甲唑-2-基）-喹喔啉衍生物，并对其生物学活性进行了评估。MTT分析表明，大多数化合物对MGC-803，HepG2，A549，HeLa，T-24和WI-38细胞系具有中等至有效的抗增殖作用。3-（苯并恶唑-2-基）-2-（N-3-二甲基氨基丙基）氨基喹喔啉（12a）表现出最强的细胞毒性，IC 50对五种测试的癌症和一种正常细胞系的免疫反应值介于1.49至10.99μM之间。琼脂糖凝胶电泳分析表明12a不会与完整的DNA相互作用，而是通过Topo I介导的DNA释放来强烈抑制拓扑异构酶I（Topo I），从而发挥其抗癌活性。分子模型研究表明12a采用独特的模式与DNA和Topo I相互作用。对MG