ethyl 2-hydroxyimino-2-(2-pyridyl)acetate | 71721-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 2-hydroxyimino-2-(2-pyridyl)acetate
• 英文别名: Hydroxyimino-pyridin-2-yl-acetic acid ethyl ester；ethyl 2-hydroxyimino-2-pyridin-2-ylacetate
• CAS: 71721-67-0
• 化学式: C₉H₁₀N₂O₃
• 分子量: 194.19
• InChiKey: YGQZRRVGGCVMQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  5

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetate
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 2-(N-hydroxyimino)-2-(pyridin-2-yl)acetate
CAS number: 71721-67-0

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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, refrigerated.
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: C9H10N2O3
Molecular weight: 194.2

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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：

  ethyl 2-hydroxyimino-2-(2-pyridyl)acetate 在 5%-palladium/activated carbon 、 三乙胺 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 11.0h， 生成 3-[4-(Trifluoromethyl)phenyl]imidazo[1,5-a]pyridine-1-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of imidazo[1,5-a]pyridine–PBD conjugates as potential DNA-directed alkylating agents

  摘要：

  一系列新型的咪唑[1,5-a]吡啶–PBD结合物被合成并评估了其在乳腺癌细胞系（MCF-7）中的抗肿瘤活性。有趣的是，所有化合物都表现出增强的DNA结合能力。这些结合物通过MTT细胞增殖实验显示出显著的抗肿瘤活性，其中化合物13f和13g表现出良好的抗肿瘤活性。处理乳腺癌细胞（MCF-7）时，使用2 μM浓度的这些化合物观察到了G2/M期细胞周期停滞。此外，当其浓度增加到4 μM时，观察到细胞在G0（凋亡）期的积累。这些化合物还诱导了参与凋亡和DNA损伤的蛋白质的表达，如p53、p21和γ-H2AX。对化合物13g与DNA的结合进行的计算机模拟结合研究帮助我们理解了相互作用的模式，我们观察到化合物13g与DNA小沟结合良好。

  DOI：

  10.1039/c2md20219k
• 作为产物：
  描述：

  2-吡啶乙酸乙酯 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.83h， 以83%的产率得到ethyl 2-hydroxyimino-2-(2-pyridyl)acetate
  参考文献：
  名称：

  咪唑并吡啶基-1,3,4-恶二唑共轭物作为细胞凋亡诱导剂和拓扑异构酶IIα抑制剂的合成及生物学评价

  摘要：

  合成了一系列咪唑并吡啶基-1,3,4-恶二唑共轭物并研究了它们的细胞毒活性，一些化合物显示出有希望的细胞毒活性。化合物8q（NSC：763639）在所有人类癌细胞系上均显示出显着的生长抑制作用，该抑制作用满足单剂量（10μM）时的阈值标准。在五个剂量水平（0.01、0.1、1、10和100μM）下进一步评估了该化合物的GI 50值，范围为1.30至5.64μM。流式细胞仪分析显示化合物8q阻止A549细胞进入亚G1期，然后诱导细胞凋亡，膜联蛋白-V-FITC，Hoechst核染色，半胱天冬酶3激活，线粒体膜电位和ROS生成进一步证实了这一点。Topo II介导的DNA弛豫分析结果表明，缀合物8q可以显着抑制topo II的活性。此外，分子对接研究还表明与拓扑异构酶（PDBID 1ZXN）结合。

  DOI：

  10.1016/j.bioorg.2016.09.002

文献信息

• Heterocycles from amino acids. A novel synthetic approach for imidazo[1,5-<i>a</i>]pyridines and imidazo[1,5-<i>a</i>]quinolines
  作者：Patrik Kolar、Andrej Petrič、Miha Tišler、Fulvia Felluga

  DOI：10.1002/jhet.5570280712

  日期：1991.11

  From the corresponding heterocyclic amino acids 2 and 9a the heterocyclic systems imidazo[1,5-a]pyridine (3) and imidazo[1,5-a]quinoline (10) are easily accessible. From compound 7 the tricyclic system 11 was prepared and from compound 17a a pyridyl-1,2,4-triazinone (18) could be obtained.

  从相应的杂环氨基酸2和9a，可容易地获得咪唑并[1，5- a ]吡啶（3）和咪唑并[1，5- a ]喹啉（10）的杂环系统。由化合物7制备三环系统11，并由化合物17a获得吡啶基-1,2,4-丁三嗪酮（18）。
• Substituted quinoxaline derivatives as interleukin-8 receptor antagonists
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US06548499B1

  公开（公告）日：2003-04-15

  Quinoxaline compounds are described as well as methods for the preparation and pharmaceutical compositions of same, which are useful as interleukin-8 (IL-8) receptor antagonists and can be used in the treatment of a chemokine-mediated disease wherein the chemokine binds to an IL-8a (CXCR1) or b (CXCR2) receptor such as a chemokine-mediated disease selected from psoriasis, or atopic distress syndrome, arthritis, inflammatory bowel disease, Crohn's disease, ulcerative colitis, gastric ulcer, septic shock, endotoxic shock, gram-negative sepsis, toxic shock syndrome, stroke, cardiac and renal reperfusion injury, glomerulo-nephritis, or thrombosis, Alzheimer's disease, graft versus host reaction, allograft rejections, or allergic diseases.

  喹喔啉化合物以及其制备方法和药物组合物被描述，这些化合物可作为白细胞介素-8（IL-8）受体拮抗剂，并可用于治疗趋化因子介导的疾病，其中趋化因子结合到IL-8a（CXCR1）或b（CXCR2）受体，例如选自牛皮癣、特应性疾病综合征、关节炎、炎症性肠病、克罗恩病、溃疡性结肠炎、胃溃疡、脓毒性休克、内毒素休克、革兰氏阴性败血症、毒性休克综合征、中风、心脏和肾脏再灌注损伤、肾小球肾炎或血栓形成，阿尔茨海默病、移植物宿主反应、移植排斥反应或过敏性疾病的趋化因子介导的疾病。
• Compounds
  申请人：Liebeschuetz Walter John

  公开号：US20050032790A1

  公开（公告）日：2005-02-10

  Compounds of formula (I) where R 2 , each X, L, Y, Cy, Lp, D and n are as defined in the specification, are serine protease inhibitors useful as antithrombotic agents.

  式(I)的化合物中，其中R2、每个X、L、Y、Cy、Lp、D和n的定义如规范中所述，是丝氨酸蛋白酶抑制剂，可用作抗血栓剂。
• Serine protease inhibitors
  申请人：Liebeschuetz John Walter

  公开号：US06855715B1

  公开（公告）日：2005-02-15

  Compounds of formula (I) where R 2 , each X, L, Y, Cy, Lp, D and n are as defined in the specification, are serine protease inhibitors useful as antithrombotic agents.

  式(I)的化合物，其中R2，每个X，L，Y，Cy，Lp，D和n如规范中所定义，是丝氨酸蛋白酶抑制剂，可用作抗血栓剂。
• ANTIVIRAL COMPOUNDS
  申请人：Bacon Elizabeth M.

  公开号：US20140018313A1

  公开（公告）日：2014-01-16

  The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  本发明涉及抗病毒化合物、含有这种化合物的组合物、包括给予这种化合物的治疗方法，以及用于制备这种化合物的有用过程和中间体。