5-甲基吡嗪-2-碳酰肼 | 37545-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-甲基吡嗪-2-碳酰肼
• 英文名称: 5-methyl-2-pyrazinecarboxylic acid hydrazide
• 英文别名: 5-Methylpyrazine-2-carbohydrazide
• CAS: 37545-33-8
• 化学式: C₆H₈N₄O
• mdl: MFCD09742108
• 分子量: 152.156
• InChiKey: IBFMTDRAKYKXQS-UHFFFAOYSA-N

物化性质

• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  80.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Methylpyrazine-2-carbohydrazide
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: 5-Methylpyrazine-2-carbohydrazide
CAS number: 37545-33-8

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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: C6H8N4O
Molecular weight: 152.2

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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：

  5-甲基吡嗪-2-碳酰肼 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 10.0h， 生成 2-methyl-5-(4-methyl-5-methylsulfanyl-4H-[1,2,4]triazol-3-yl)pyrazine
  参考文献：
  名称：

  Synthesis, Characterization and Biological Screening of Some Novel Pyrazine Associated 1,2,4-Triazoles

  摘要：

  现已开发出一种新的高效方法，用于合成一些与吡嗪相关的新型 1,2,4-三唑，如 2-甲基-5-(4-烷基/芳基-5-甲硫基-4H-[1,2,4]-三唑-3-基)-吡嗪 (5a-c)。这种新方法涉及原料 5-甲基-2-吡嗪羧酸（1）和 5-甲基-2-吡嗪羧酸酰肼（2）、5-甲基-2-吡嗪羧酸酰肼 N-烷基/芳基硫代甲酰胺（3a-c）和 4-烷基/芳基-5-(5-甲基吡嗪-2-基)-2,4-二氢-[1,2,4]-三唑-3-硫酮（4a-c）为中间体，收率良好至极佳。通过红外光谱、1H NMR、质谱和元素分析，确定了所有这些化合物的化学结构。此外，还对目标化合物的抗菌活性进行了评估。

  DOI：

  10.14233/ajchem.2016.19860
• 作为产物：
  描述：

  5-甲基吡嗪-2-羧酸 在 硫酸 、 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 5-甲基吡嗪-2-碳酰肼
  参考文献：
  名称：

  作为阿兹海默症兰尼碱受体和乙酰胆碱酯酶双重抑制剂的腙的设计、合成和评价

  摘要：

  阿尔茨海默病 (AD) 涉及神经元丢失、斑块和神经原纤维缠结形成以及神经元 Ca 2+稳态紊乱，这会导致严重的痴呆、记忆丧失以及最终可能导致死亡的思维和行为紊乱。钙失调和低乙酰胆碱水平是阿尔茨海默病进展的两个主要机制。单分子同时抑制钙振荡（储存过载诱导的 Ca 2+释放 [SOICR]）和乙酰胆碱酯酶 (AChE) 可能为 AD 治疗带来新的希望。在这里，我们将一些丹曲林衍生物描述为兰尼碱受体和 AChE 的双重抑制剂。两个系列的芳香族酰腙/磺酰腙衍生物 组被设计和合成。在这项研究中，使用丹曲林和多奈哌齐作为阳性对照，评估了目标化合物在体外抑制 SOICR 和 AChE 的能力。化合物22a对 SOICR（抑制率 (%) = 90.1，IC 50 = 0.162 μM）和 AChE（抑制率 (%) = 93.5%，IC 50 = 0.372 μM）表现出优异且平衡的抑制效力。对接模拟表明，

  DOI：

  10.1016/j.bioorg.2023.106432

文献信息

• Pyrazine Associated Novel 1,2,4-Triazolo Thiadazines: Synthesis, Characterization and as Antibacterial Agents
  作者：Chandra Sekhara Reddi Maddireddi、Uma Devi Parimi、Sreenivasa Reddy Bhimi Reddy、Satyanarayana Reddy Mandapati

  DOI：10.14233/ajchem.2016.20011

  日期：——

  5-(5-Methyl-pyrazin-2-yl)-[1,3,4]-oxadiazole-2-thiol (4) has been synthesized form the starting material 5-methyl-2-pyrazinecarboxylic acid (1) on esterification with ethanol and condensation with hydrazine hydrate followed by cyclization with carbon disulfide. Compound 4 further converted into the next intermediate, 4-amino-5-(5-methyl-pyrazin-2-yl)-4H-[1,2,4]-triazole-2-thiol (5) when reacts with hydrazine hydrate. Finally, the target compounds, 3-(5-methyl-pyrazin-2-yl)-6-aryl-7H-[1,2,4]-triazole-[3,4-b][1,3,4]-thiadazine (6a-g) have been synthesized successfully from the condensation reaction performed using compound 5 and a variety of phenacyl bromides. The chemical structures of all the newly synthesized intermediates and products were confirmed by IR, 1H NMR, mass spectral studies and elemental analysis. Additionally all the target compounds have been screened for antibacterial activity.

  5-(5-甲基-吡嗪-2-基)-[1,3,4]-噁二唑-2-硫醇（4）已从起始原料5-甲基-2-吡嗪羧酸（1）通过与乙醇酯化、与水合肼缩合，随后与二硫化碳环化合成。化合物4与水合肼反应进一步转化为下一个中间体，4-氨基-5-(5-甲基-吡嗪-2-基)-4H-[1,2,4]-三唑-2-硫醇（5）。最终，通过化合物5与多种苯乙酰溴的缩合反应成功合成了目标化合物，3-(5-甲基-吡嗪-2-基)-6-芳基-7H-[1,2,4]-三唑-[3,4-b][1,3,4]-噻二嗪（6a-g）。所有新合成的中间体和产物的化学结构均通过IR、1H NMR、质谱研究及元素分析得到确认。此外，所有目标化合物均进行了抗菌活性筛选。
• [EN] TETRAZOLE DERIVATIVES AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS (MGLURS)<br/>[FR] DÉRIVÉS DE TÉTRAZOLE UTILES COMME MODULATEURS DES RÉCEPTEURS MÉTABOTROPES DU GLUTAMATE
  申请人：ASTRAZENECA AB

  公开号：WO2009051556A1

  公开（公告）日：2009-04-23

  The present invention relates to compounds of formula (I), their use for the manufacture of a medicament for the treatment of a mGluR5 receptor-mediated disorder. Formula (I) wherein. R1 is, or.

  本发明涉及公式（I）的化合物，其用于制造治疗mGluR5受体介导的疾病的药物。其中，公式（I）中R1是，或。
• [EN] USE OF NEW LIPOXYGENASE INHIBITORS<br/>[FR] UTILISATION DE NOUVEAUX INHIBITEURS DE LIPOXYGENASE
  申请人：BIOLIPOX AB

  公开号：WO2005084656A1

  公开（公告）日：2005-09-15

  There is provided a use of a compound of formula (I), wherein R<1>, R<2>, R<3 >and R<4> have meanings given in the description, and pharmaceutically-acceptable salts thereof, for the manufacture of a medicament for the treatment of a disease in which inhibition of the activity of a lipoxygenase (e.g. 15-lipoxygenase) is desired and/or required, and particularly in the treatment of inflammation.

  提供了一种化合物（I）的用途，其中R1、R2、R3和R4的含义如描述中所示，并且其药用可接受的盐，用于制造一种药物，用于治疗需要或要求抑制脂氧化酶（例如15-脂氧化酶）活性的疾病，特别是在治疗炎症方面。
• Synthesis and docking studies of pyrazine–thiazolidinone hybrid scaffold targeting dormant tuberculosis
  作者：T.S. Chitre、K.D. Asgaonkar、P.B. Miniyar、A.B. Dharme、M.A. Arkile、A. Yeware、D. Sarkar、V.M. Khedkar、P.C. Jha

  DOI：10.1016/j.bmcl.2016.03.055

  日期：2016.5

  against current antimycobactrial drugs. To address this issue, we report herein the synthesis of N-(4-oxo-2 substituted thiazolidin-3yl) pyrazine-2-carbohydrazide derivatives designed by following the molecular hybridization approach using pyrazine and thiazolidenone scaffolds. The compounds were evaluated against MTB H37Ra and Mycobacterium bovis BCG in dormancy model. Most of the compounds had IC50

  结核分枝杆菌（MTB）处于休眠期的持久性有助于病原体对当前的抗分枝杆菌药物产生耐药性。为了解决这个问题，我们在本文中报道了通过使用吡嗪和噻唑烯酮支架的分子杂交方法设计的N-（4-氧代-2取代的噻唑烷-3基）吡嗪-2-碳酰肼衍生物的合成。在休眠模型中，针对MTB H37Ra和牛分枝杆菌BCG对化合物进行了评估。大多数化合物的IC 50值在0.3–1μg/ ml范围内。使用MTT测定法进一步测试了活性化合物对THP-1，Panc-1，A549和MCF-7细胞系的抗增殖活性，并且没有显示出明显的细胞毒性。我们还报告了使用活性类似物和MTB-癸烯基磷酸基-β- d-核糖-2'-表异构酶（DprE1）进行的分子对接研究，以合理化生物学活性，并提供有关杂化结构的可能作用机理和结合模式的见解。获得的结果验证了分子杂交方法的使用，并且还表明所报道的化合物可以提供一种新颖的药效团来合成针对dormat MTB的先导化合物。
• Use of New Lipoxygenase Inhibitors
  申请人：Olofsson Kristofer

  公开号：US20080227787A1

  公开（公告）日：2008-09-18

  There is provided a use of a compound of formula (I), wherein R 1 , R 2 , R 3 and R 4 have meanings given in the description, and pharmaceutically-acceptable salts thereof, for the manufacture of a medicament for the treatment of a disease in which inhibition of the activity of a lipoxygenase (e.g. 15-lipoxygenase) is desired and/or required, and particularly in the treatment of inflammation.

  提供了一种化合物（I）的用途，其中R1，R2，R3和R4具有描述中给出的含义，并且其药学上可接受的盐，用于制造治疗疾病的药物，在该疾病中，需要和/或期望抑制脂氧化酶（例如15-脂氧化酶）的活性，特别是在治疗炎症方面。