2-(2-氨基噻唑-4-基)乙醛酸乙酯 | 64987-08-2

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(2-氨基噻唑-4-基)乙醛酸乙酯
• 中文别名: 乙酯2-(2-氨基噻唑-4-基)乙醛酸；2-氨基-4-噻唑乙醛酸乙酯；氨基噻唑乙醛酸乙酯；2-(2-氨基-4-噻唑基)-2-氧代乙酸乙酯
• 英文名称: ethyl 2-(2-aminothiazol-4-yl)glyoxylate
• 英文别名: ethyl 2-(2-aminothiazol-4-yl)-2-oxoacetate；2-(amino-thiazol-4-yl)-oxo-acetic acid ethyl ester；ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetate
• CAS: 64987-08-2
• 化学式: C₇H₈N₂O₃S
• mdl: MFCD00010414
• 分子量: 200.218
• InChiKey: XNVRKLCQBZTGNA-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C(lit.)
• 沸点：
  361.6±15.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2934100090
• 安全说明：
  S26,S37/39
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 2-(2-aminothiazol-4-yl)glyoxylate
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-(2-aminothiazol-4-yl)glyoxylate
CAS number: 64987-08-2

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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, 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: C7H8N2O3S
Molecular weight: 200.2

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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, sulfur 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

制备方法与用途

用途：用于生产头孢类药物的中间体

反应信息

• 作为反应物：
  描述：

  2-(2-氨基噻唑-4-基)乙醛酸乙酯 在 吡啶 、 4-二甲氨基吡啶 、 三氧化硫吡啶 、 三氯化硼 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 对二甲苯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 78.0h， 生成 4-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2R,3S)-2-[[(1,5-dihydroxy-4-oxopyridin-2-yl)methylcarbamoylamino]methyl]-4-oxo-1-sulfoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxybutanoic acid
  参考文献：
  名称：

  Pyridone-Conjugated Monobactam Antibiotics with Gram-Negative Activity

  摘要：

  Herein we describe the structure-aided design and synthesis of a series of pyridone-conjugated monohactam analogues with in vitro, antibacterial activity against clinically relevant Grain-negative species including Pseuedomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli. Rat pharmacokinetic studies with,compound 17 demonstrate low clearance and low plasma protein binding. In addition evidence is provided for a number of analogues suggesting that the siderophore receptors PiuA and PirA play a role in drug uptake in P. aeruginosa strain PAO1.

  DOI：

  10.1021/jm400560z
• 作为产物：
  描述：

  去甲氨噻肟酸乙酯 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 正己烷 、 二氯甲烷 、 sodium carbonate 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 生成 2-(2-氨基噻唑-4-基)乙醛酸乙酯
  参考文献：
  名称：

  Cephalosporins with sulfur-containing oxyimino side chain

  摘要：

  公式为##STR1##的抗菌化合物，其中R是单核碳环芳基，含有氧或硫原子或亚胺或较低烷基亚胺基作为杂环（非碳）环成员的5-成员芳香杂环基，可选地，一个或两个氮原子，或者含有一个到三个氮原子作为杂环环成员的6-成员芳香杂环基；R.sup.1是氢或在头孢菌素化学中可用的3-取代基；A是较低烷基或可选地取代有羧基、氨基甲酰基、较低烷基氨基甲酰基或二（较低烷基）氨基甲酰基的C.sub.3-7-环烷基；Q是较低烷基或可选地取代有羧基、氨基甲酰基、较低烷基氨基甲酰基或二（较低烷基）氨基甲酰基的C.sub.3-7-环烷基，或者是基团--NR.sup.2--或--NR.sup.2 NR.sup.3--；R.sup.2和R.sup.3独立地是氢或较低烷基；p和m为零或1，n为零、1或2；R.sup.4是氢、较低烷酰基或三（较低烷基）硅基；两个R.sup.4基团一起代表二苯甲亚甲基；R.sup.5是氢、较低烷基、羟基、较低烷氧基、卤素、硝基、--OCOR.sup.7、--OCOOR.sup.71、--N(R.sup.7).sub.2、--NHCOR.sup.7、--NHCOOR.sup.71、--COR.sup.7、--SR.sup.7、--SOR.sup.7、--SO.sub.2 R.sup.7、--SO.sub.3 H、--COOR.sup.7或--CON(R.sup.7).sub.2；R.sup.6是氢、较低烷基或卤素，R.sup.7是氢或较低烷基；R.sup.71是较低烷基，两个--OR.sup.4基团通过相邻碳原子连接到苯环上，以及这些化合物的容易水解的酯和药用可接受盐以及公式I的化合物和其酯和盐的水合物。

  公开号：

  US05036064A1
• 作为试剂：
  描述：

  溴乙酰乙醛酸乙酯 、 硫脲 、 甲烷 在 碳酸氢钠 、 2-(2-氨基噻唑-4-基)乙醛酸乙酯 作用下， 以 水 、 乙醇 为溶剂， 反应 1.0h， 生成 2-(2-氨基噻唑-4-基)乙醛酸乙酯
  参考文献：
  名称：

  Cephem derivatives and processes for their manufacture

  摘要：

  该专利涉及一种通用式为##STR1##中R.sub.2 O基位于同构位的头孢菌素衍生物，其制备方法以及含有这些化合物并对抗细菌感染的药物配方。

  公开号：

  US05710146A1

文献信息

• [EN] BICYCLIC ARYL MONOBACTAM COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS D'ARYLMONOBACTAME BICYCLIQUES ET LEURS MÉTHODES D'UTILISATION POUR LE TRAITEMENT DES INFECTIONS BACTÉRIENNES
  申请人：MERCK SHARP & DOHME

  公开号：WO2017155765A1

  公开（公告）日：2017-09-14

  The present invention relates to bicyclic aryl monobactam compounds of Formula (I), and pharmaceutically acceptable salts thereof, wherein A1, L, M, W, X, Y, Z, RX and Rz are as defined herein. The present invention also relates to compositions which comprise a bicyclic aryl monobactam compound of the invention or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. The invention further relates to methods for treating a bacterial infection comprising administering to the patient a therapeutically effective amount of a compound of the invention, either alone or in combination with a therapeutically effective amount of one or more beta-lactamase inhibitor compounds.

  本发明涉及公式（I）的双环芳基单β内酰胺化合物及其药学上可接受的盐，其中A1、L、M、W、X、Y、Z、RX和Rz如本文所定义。本发明还涉及包含本发明的双环芳基单β内酰胺化合物或其药学上可接受的盐以及药学上可接受的载体的组合物。该发明还涉及治疗细菌感染的方法，包括向患者施用本发明化合物的治疗有效量，单独或与一种或多种β-内酰胺酶抑制剂化合物的治疗有效量结合使用。
• Heteroaromatic glucokinase activators
  申请人：——

  公开号：US20010039344A1

  公开（公告）日：2001-11-08

  2,3-Di-substituted N-heteroaromatic propionamides with said substitution at the 2-position being a substituted phenyl group and at the 3-position being a cycloalkyl ring, said propionamides being glucokinase activators which increase insulin secretion in the treatment of type II diabetes.

  2,3-二取代N-杂环丙酰胺，其中2-位取代为取代苯基，3-位取代为环烷基环，这些丙酰胺是葡萄糖激酶激活剂，可增加胰岛素分泌，用于治疗2型糖尿病。
• Substituted hydantoins
  申请人：Chu Xin-Jie

  公开号：US20060041146A1

  公开（公告）日：2006-02-23

  The present invention relates to compounds of the formula which are useful in treating diseases characterized by the hyperactivity of MEK. Accordingly the compounds are useful in the treatment of diseases, such as, cancer, cognative and CNS disorders and inflammatory/autoimmune diseases.

  本发明涉及一类化合物，其结构式如下： 这些化合物在治疗由MEK过度活跃引起的疾病方面具有用途。因此，这些化合物在治疗诸如癌症、认知和CNS疾病以及炎症/自身免疫疾病等疾病方面是有用的。
• Iron‐Enabled Utilization of Air as the Terminal Oxidant Leading to Aerobic Oxidative Deoximation by Organoselenium Catalysis
  作者：Chao Chen、Xu Zhang、Hongen Cao、Fang Wang、Lei Yu、Qing Xu

  DOI：10.1002/adsc.201801163

  日期：2019.2

  spectroscopy (XPS) analysis suggest that iron is crucial in the catalytic cycle, working to prohibit the deactivation of selenium catalyst through an iron‐catalyzed aerobic oxidation of low valent selenium species by air to the active high valent selenium species. Since air can be utilized as the terminal oxidant, this work may contribute to the advance of organoselenium catalysis.

  与需要过氧化物氧化剂（例如过氧化氢）的常规有机硒催化氧化反应相反，在这项工作中，我们发现，添加低含量的铁（II）可以使空气成功地用作有机硒催化的末端氧化剂酮肟的氧化脱氧反应。这导致了一种新的温和且相对绿色的好氧氧化脱氧方法。控制反应和X射线光电子能谱（XPS）分析表明，铁在催化循环中至关重要，它通过空气将低价硒物种通过铁催化有氧氧化为活性高价硒而阻止硒催化剂失活。物种。由于可以将空气用作末端氧化剂，因此这项工作可能有助于有机硒催化的发展。
• NOVEL CEPHALOSPORIN DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF
  申请人：CHO Young Lag

  公开号：US20120264727A1

  公开（公告）日：2012-10-18

  The present invention relates to novel cephalosporin derivatives represented by Chemical Formula 1. Wherein, X, Y, L, R 1 , and R 2 are as same as defined in the description of the invention. The present invention also relates to pharmaceutical antibiotic compositions comprising a novel celphalosporin derivative represented by Chemical Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an effective ingredient. According to the present invention, novel cephalosporin derivatives, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an effective ingredient for the broad spectrum of antibiotic resistant, low toxicity, particularly in Gram-negative bacteria, which can be useful with strong antimicrobial activity.

  本发明涉及由化学公式1表示的新型头孢菌素衍生物。其中，X、Y、L、R1和R2与发明描述中定义的相同。本发明还涉及包含由化学公式1表示的新型头孢菌素衍生物、前药、水合物、溶剂化物、异构体或药用可接受盐作为有效成分的药物抗生素组合物。根据本发明，新型头孢菌素衍生物、前药、水合物、溶剂化物、异构体或药用可接受盐作为广谱抗生素耐药、低毒性的有效成分，特别是在革兰氏阴性细菌中，可以具有强大的抗菌活性。