2-氨基-3-羟基吡嗪 | 43029-19-2

• 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: 2-氨基-3-羟基吡嗪
• 中文别名: 3-氨基-2-羟基吡嗪；2-羟基-3-氨基吡嗪；3-氨基吡嗪-2(3H)-酮
• 英文名称: 3-aminopyrazin-2(1H)-one
• 英文别名: 3-Aminopyrazin-2-ol；3-amino-1H-pyrazin-2-one
• CAS: 43029-19-2
• 化学式: C₄H₅N₃O
• 分子量: 111.103
• InChiKey: KQLHRXQKORXSTC-UHFFFAOYSA-N

物化性质

• 熔点：
  300-301℃
• 密度：
  1.55

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Amino-2(1h)-pyrazinone
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: 3-Amino-2(1h)-pyrazinone
CAS number: 43029-19-2

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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: C4H5N3O
Molecular weight: 111.1

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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：

  2-氨基-3-羟基吡嗪 在 三氯氧磷 作用下， 生成 2-氯-3-氨基吡嗪
  参考文献：
  名称：

  Pyrazine Chemistry. II. Derivatives of 3-Hydroxypyrazionic Acid

  摘要：

  DOI：

  10.1021/ja01197a017
• 作为产物：
  描述：

  2-amino-3-azidopyrazine 在 盐酸 、 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以91%的产率得到2-氨基-3-羟基吡嗪
  参考文献：
  名称：

  Studies on Pyrazines; Part 30:¹Synthesis of Aminopyrazines from Azidopyrazines

  摘要：

  叠氮吡嗪不能通过有效制备烷基或芳基胺的试剂进行还原，因为杂环叠氮化物以双环形式存在于四唑[1,5-a]吡嗪中。然而，通过在氨 hydroxide 和钯-炭存在下进行加氢裂解，或通过在醇溶盐酸中用氯化锡(II)还原，成功转化为氨基吡嗪，产率为34-87%。为了阐明反应的成功进展，通过1H NMR光谱在不同溶剂中检查了叠氮-四唑的平衡。

  DOI：

  10.1055/s-1994-25607

文献信息

• Discovery of pyrimidine nucleoside dual prodrugs and pyrazine nucleosides as novel anti-HCV agents
  作者：Shuang Guo、Mingshuo Xu、Qi Guo、Fuqiang Zhu、Xiangrui Jiang、Yuanchao Xie、Jingshan Shen

  DOI：10.1016/j.bmc.2019.01.007

  日期：2019.3

  metabolized in human liver microsomes expectantly. On the other hand, aiming to discover novel anti-HCV nucleosides, pyrazin-2(1H)-one nucleosides and their phosphoramidate prodrugs were investigated. Several active compounds were discovered, such as 25e (EC50 = 7.3 μM) and S-29b (EC50 = 19.5 μM). This kind of nucleosides were interesting and would open a new avenue for the development of antiviral agents

  为了探索双重前药策略在开发抗HCV药物中的应用潜力，设计并合成了在尿嘧啶部分的C4或N3位置修饰的多种Sofosbuvir衍生物。在基于基因型1b的复制子Huh-7细胞系中，某些化合物表现出有效的抗HCV活性，例如4e和8a-8c具有与sofosbuvir相似的EC50值（0.20-0.22μM）（EC50 = 0.18μM）。此外，8b表现出良好的人血浆稳定性，并且预期在人肝微粒体中容易被代谢。另一方面，为了发现新颖的抗HCV核苷，对吡嗪-2（1H）-一核苷及其氨基磷酸酯前药进行了研究。发现了几种活性化合物，例如25e（EC50 = 7.3μM）和S-29b（EC50 = 19.5μM）。
• [EN] COMPOSITIONS AND METHODS FOR TREATMENT OF CORONAVIRUS INFECTION<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT D'UNE INFECTION À CORONAVIRUS
  申请人：CORTEXYME INC

  公开号：WO2022066776A1

  公开（公告）日：2022-03-31

  Compounds and methods for the treatment of coronavirus infections are disclosed. Compounds according to Formula I as described herein, containing reactive functional groups for covalent binding to active site residues in target proteases, can be used for treating infection by SARS-CoV-2 and other coronaviruses.

  本文披露了用于治疗冠状病毒感染的化合物和方法。根据本文描述的Formula I的化合物，其中含有可与靶蛋白酶活性位点残基发生共价结合的反应性功能基团，可用于治疗SARS-CoV-2和其他冠状病毒感染。
• [EN] DIHYDROQUINAZOLIN-2-ONE DERIVATIVES AS SELECTIVE CYTOTOXIC AGENTS USEFUL IN THE TREATMENT OF HIV<br/>[FR] DÉRIVÉS DE DIHYDROQUINAZOLIN-2-ONE EN TANT QU'AGENTS CYTOTOXIQUES SÉLECTIFS UTILES DANS LE TRAITEMENT DU VIH
  申请人：MERCK SHARP & DOHME

  公开号：WO2022046844A1

  公开（公告）日：2022-03-03

  The present disclosure is directed to tetrahydroquinazoline derivatives of Formula I and their use for selectively killing HIV infected GAG-POL expressing cells without concomitant cytotoxicity to HIV naïve cells, and for the treatment or prophylaxis of infection by HIV, or for the treatment, prophylaxis or delay in the onset or progression of AIDS or AIDS Related Complex (ARC).

  本公开涉及公式I的四氢喹噁啉衍生物及其用于选择性杀灭HIV感染的GAG-POL表达细胞，而不对HIV天然细胞产生细胞毒性，以及用于治疗或预防HIV感染，或用于治疗、预防或延缓艾滋病或艾滋病相关综合征（ARC）的发病或进展。
• Synthesis of an N-aminopyrazinonium analog of cytidine
  作者：Tzoong Chyh Lee、Paul L. Chello、Ting Chao Chou、Mary Agnes Templeton、James C. Parham

  DOI：10.1021/jm00356a033

  日期：1983.2

  An N-aminated pyrazine analogue of cytidine, in which the pyrimidine N(3) ring nitrogen and C(4) amino group were replaced by a C-amino and an N-amino function, respectively, was prepared as a potential deaminase-resistant cytidine antimetabolite. The nucleoside 1,2-diamino-4-beta-D-ribofuranosylpyrazin-2-onium chloride (6) was a mild cytostatic agent but was neither a substrate for nor an inhibitor

  胞嘧啶的N-氨基吡嗪类似物，其中嘧啶N（3）环氮和C（4）氨基分别被C-氨基和N-氨基官能团取代，被制备为潜在的脱氨酶耐药性胞苷抗代谢药。核苷1,2-二氨基-4-β-D-呋喃呋喃糖基吡嗪-2-氯化铵（6）是一种温和的细胞抑制剂，但既不是小鼠肾胞苷脱氨酶的底物也不是其抑制剂。它以比预期更低的pKa电离。该阴离子没有经历通常在N-亚氨基杂环基团上观察到的二聚反应，但是没有经过2-氨基的水解以产生1-氨基吡嗪-2,3-二酮核苷。
• 螺环类化合物、其制备方法及其用途
  申请人：上海柯君医药科技有限公司

  公开号：CN117820325A

  公开（公告）日：2024-04-05

  本发明公开一种螺环类化合物、其制备方法及其用途。本发明的螺环类化合物为如式I所示化合物或其药学上可接受的盐。本发明化合物具备相当或更优的主蛋白酶活性抑制能力和更好的氧化酶耐受能力，实现了很好的抗冠状病毒活性和优异的人肝微粒体稳定性，临床使用中无需与利托那韦等连用，在体内具有更长的氧化代谢时间，减少每日口服次数，有利于提升药物依从性。#imgabs0#