乙基胺基噻唑 | 64987-03-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 乙基胺基噻唑
• 中文别名: 2-甲酰氨基噻唑-4-乙醛酸乙酯；甲酰氨基噻唑乙醛酸乙酯
• 英文名称: ethyl 2-(formylamino)-4-thiazoleglyoxylate
• 英文别名: ethyl 2-(2-formylaminothiazol-4-yl)glyoxylate；(2-formylamino-thiazol-4-yl)-oxo-acetic acid ethyl ester；ethyl 2-formamido-α-oxothiazol-4-acetate；ethyl (2-formamido-1,3-thiazol-4-yl)(oxo)acetate；ethyl 2-(2-formamido-1,3-thiazol-4-yl)-2-oxoacetate
• CAS: 64987-03-7
• 化学式: C₈H₈N₂O₄S
• mdl: MFCD00010412
• 分子量: 228.229
• InChiKey: NTACMHVXGGGRQU-UHFFFAOYSA-N

物化性质

• 熔点：
  232-234 °C
• 沸点：
  381.3±34.0 °C(Predicted)
• 密度：
  1.5150 (rough estimate)
• 溶解度：
  可溶于氯仿（轻微、加热）、DMSO（轻微）
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2934100090
• 危险品运输编号：
  OTH
• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319

SDS

Name:	Ethyl 2-(Formylamino)-4-Thiazoleglyoxylate 99% Material Safety Data Sheet
Synonym:	None
CAS:	64987-03-7

Section 1 - Chemical Product MSDS Name:Ethyl 2-(Formylamino)-4-Thiazoleglyoxylate 99% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
64987-03-7	Ethyl 2-(Formylamino)-4-Thiazoleglyoxy	99%	265-299-4

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 64987-03-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Decomposes
Freezing/Melting Point: 231 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: > 237 deg C
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H8N2O4S
Molecular Weight: 228.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 64987-03-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2-(Formylamino)-4-Thiazoleglyoxylate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 64987-03-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 64987-03-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 64987-03-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

乙基胺基噻唑可用作有机合成中间体，在实验室研发和化工医药合成过程中发挥作用。

制备

将四水合乙酸亚乙酯（120克）、乙酸（1000毫升）及乙酸酐（100毫升）的混合物置于130℃至135℃的油浴中搅拌20分钟。随后，在105℃至110℃下继续搅拌，于5分钟内分批加入高锰酸钾（20克），然后将混合物在130℃至135℃下进一步搅拌30分钟。冷却至室温后，加入2-（2-甲酰氨基噻唑-4-基）乙酸乙酯（53.5克）。接下来，在38℃至40℃条件下以6000毫升的速率进行空气搅拌15小时。反应结束后，过滤并收集沉淀物，然后依次用乙酸和水洗涤，并干燥得到2-（2-甲酰氨基噻唑-4-基）乙醛酸乙酯（即乙基胺基噻唑），其熔点为232-233℃（分解）。

反应信息

• 作为反应物：
  描述：

  乙基胺基噻唑 在 盐酸 、 sodium hydroxide 、 三甲基氯硅烷 、 氯化亚砜 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (6R)-7t-[2-(2-amino-thiazol-4-yl)-2-oxo-acetylamino]-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of a new class of 2-(2-aminothiazol-4-yl)-2-hydrazonoacetamido cephalosporins

  摘要：

  A series of 2-(2-aminothiazol-4-yl)-2-hydrazonoacetamido cephalosporins 1a-h was prepared. Whenever possible, E and Z isomers were isolated, and their relative stabilities and their interconversions were tested. The antibacterial activity was tested against Gram-positive and Gram-negative bacteria. For compound 1c, whose Z and E forms do not interconvert rapidly, the Z form was the more active one. Among the other compounds, for which the E form is the only stable one for practical purposes, compound 1a was the most active. When compared with cefuroxime and cefotaxime, compound 1a showed slightly lower antibacterial activity but good serum level and half-life values.

  DOI：

  10.1021/jm00388a003
• 作为产物：
  描述：

  甲酰氨基噻唑乙酸乙酯 在 N-羟基邻苯二甲酰亚胺 、 氧气 、 cobalt(II) acetate 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 以21%的产率得到乙基胺基噻唑
  参考文献：
  名称：

  N-羟基邻苯二甲酰亚胺/钴（II）分子氧催化低温苯氧化

  摘要：

  通过用分子氧和N-羟基邻苯二甲酰亚胺/乙酸钴（II）作为催化剂直接氧化相应的芳酯酸酯或扁桃酸酯，在非常温和的条件下以良好或优异的收率形成了多种（取代的）芳基乙醛酸酯。杂芳族类似物更难被该系统氧化。研究了N-羟基邻苯二甲酰亚胺芳环上的取代对乙苯氧化的影响。吸电子取代基加速乙苯的氧化并促进苯乙酮的形成。给电子取代基导致降低的氧化速率并增强了对1-苯基乙醇的选择性。

  DOI：

  10.1016/s0040-4020(00)00679-7

文献信息

• QUINOXALINYL DIPEPTIDE HEPATITIS C VIRUS INHIBITORS
  申请人：Gai Yonghua

  公开号：US20080267918A1

  公开（公告）日：2008-10-30

  The present invention relates to compounds of Formula I, or a pharmaceutically acceptable salt, ester, or prodrug, thereof: which inhibit serine protease activity, particularly the activity of hepatitis C virus (HCV) NS3-NS4A protease. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明涉及式I化合物，或其药用可接受的盐、酯或前药： 其抑制丝氨酸蛋白酶活性，尤其是丙型肝炎病毒（HCV）NS3-NS4A蛋白酶的活性。因此，本发明的化合物干扰丙型肝炎病毒的生命周期，并且还可用作抗病毒剂。本发明进一步涉及包含前述化合物的药物组合物，用于给患有HCV感染的对象服用。本发明还涉及通过管理包含本发明化合物的药物组合物来治疗主体中的HCV感染的方法。
• [EN] QUINOXALINE-CONTAINING COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS<br/>[FR] COMPOSÉS CONTENANT DE LA QUINOXALINE EN TANT QU'INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：ENANTA PHARM INC

  公开号：WO2009064975A1

  公开（公告）日：2009-05-22

  The present invention discloses compounds of formula I and II or pharmaceutically acceptable salts, esters, or prodrugs thereof which inhibit serine protease activity, particularly the activity of hepatitis C virus (HCV) NS3-NS4A protease. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明公开了抑制丝氨酸蛋白酶活性的I和II公式化合物，或其药物可接受的盐、酯或前药，尤其是抑制丙型肝炎病毒（HCV）NS3-NS4A蛋白酶的活性。因此，本发明的化合物干扰丙型肝炎病毒的生命周期，并且也用作抗病毒剂。本发明进一步涉及包含前述化合物的药物组合物，用于给患有HCV感染的主体进行管理。本发明还涉及通过管理包含本发明化合物的药物组合物来治疗主体中的HCV感染的方法。
• Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors
  申请人：——

  公开号：US20040266668A1

  公开（公告）日：2004-12-30

  The present invention relates to compounds of Formula I or II, or a pharmaceutically acceptable salt, ester, or prodrug, thereof: 1 which inhibit serine protease activity, particularly the activity of hepatitis C virus (HCV) NS3-NS4A protease. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明涉及式I或II的化合物，或其药学上可接受的盐、酯或前药：1，其抑制丝氨酸蛋白酶活性，特别是乙型肝炎病毒（HCV）NS3-NS4A蛋白酶的活性。因此，本发明的化合物干扰乙型肝炎病毒的生命周期，并且也可用作抗病毒剂。本发明还涉及含有上述化合物的药物组合物，用于治疗患有HCV感染的受试者。该发明还涉及通过给受试者投予含有本发明化合物的药物组合物来治疗HCV感染的方法。
• Quinoxalinyl Macrocyclic Hepatitis C Virus Serine Protease Inhibitors
  申请人：Niu Deqiang

  公开号：US20070299078A1

  公开（公告）日：2007-12-27

  The present invention relates to compounds, including compounds of Formula I, or a pharmaceutically acceptable salt, ester, or prodrug, thereof: which inhibit serine protease activity, particularly the activity of hepatitis C virus (HCV) NS3-NS4A protease. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明涉及化合物，包括式I的化合物，或其药用可接受的盐、酯或前药：这些化合物抑制丝氨酸蛋白酶活性，特别是丝氨酸蛋白酶活性，尤其是丙型肝炎病毒（HCV）NS3-NS4A蛋白酶的活性。因此，本发明的化合物干扰丙型肝炎病毒的生命周期，并且还可用作抗病毒药剂。本发明还涉及包含上述化合物的药物组合物，用于治疗患有HCV感染的受试者。该发明还涉及通过给予含有本发明化合物的药物组合物来治疗受试者的HCV感染的方法。
• Quinoxalinyl tripeptide hepatitis C virus inhibitors
  申请人：Gai Yonghua

  公开号：US20080032936A1

  公开（公告）日：2008-02-07

  The present invention relates to compounds of Formula I, or a pharmaceutically acceptable salt, ester, or prodrug, thereof: which inhibit serine protease activity, particularly the activity of hepatitis C virus (HCV) NS3-NS4A protease. Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明涉及式I的化合物，或其药用可接受的盐、酯或前药，其抑制丝氨酸蛋白酶活性，特别是乙型肝炎病毒（HCV）NS3-NS4A蛋白酶的活性。因此，本发明的化合物干扰了乙型肝炎病毒的生命周期，同时也可用作抗病毒药物。本发明还涉及包含上述化合物的药物组合物，用于治疗患有HCV感染的受试者。该发明还涉及通过给受试者投与含本发明化合物的药物组合物来治疗HCV感染的方法。