5-氨基-1-甲基吡唑-4-甲酸 | 4058-91-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1-甲基吡唑-4-甲酸
• 中文别名: 1-甲基-5-氨基吡唑-4-甲酸
• 英文名称: 1-methyl-5-amino-1H-pyrazole-4-carboxylic acid
• 英文别名: 5-amino-1-methyl-1H-pyrazole-4-carboxylic acid；5-amino-1-methyl-1H-pyrazole-4-carboxylic acid；1-Methyl-5-amino-4-pyrazolcarbonsaeure；1-Methyl-5-aminopyrazol-4-carbonsaeure；5-amino-1-methylpyrazole-4-carboxylic acid
• CAS: 4058-91-7
• 化学式: C₅H₇N₃O₂
• mdl: MFCD00973833
• 分子量: 141.129
• InChiKey: NVRCXLPKLCKSSN-UHFFFAOYSA-N

物化性质

• 沸点：
  371.3±27.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Amino-1-methyl-1H-pyrazole-4-carboxylic acid
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-Amino-1-methyl-1H-pyrazole-4-carboxylic acid
CAS number: 4058-91-7

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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: C5H7N3O2
Molecular weight: 141.1

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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：

  5-氨基-1-甲基吡唑-4-甲酸 在 tetrafluoroboric acid 、 sodium nitrite 、 铜 作用下， 以 水 为溶剂， 生成 1-甲基-5-硝基吡唑-4-甲酸
  参考文献：
  名称：

  PF-04859989作为基于结构的药物设计的模板：鉴定具有改善的亲脂性效率的新型吡唑系列不可逆KAT II抑制剂

  摘要：

  本文描述了新的吡唑系列不可逆KAT II抑制剂的基于结构的设计，合成和生物学评估。从二氢喹啉酮核心到四氢吡唑并吡啶并酮核心的1和2抑制剂骨架的修饰导致发现了一系列新的有效KAT II抑制剂，这些抑制剂具有出色的理化性质。在这些新的吡唑类似物中，化合物20是最有效和亲脂性最强的化合物，其k inact / K i值为112,000 M -1  s -1，亲脂性效率（LipE）为8.53。X射线晶体结构为20 KAT II的使用证明了有助于实现这种非凡效能和结合效率的关键功能。

  DOI：

  10.1016/j.bmcl.2013.02.039
• 作为产物：
  描述：

  5-氨基-1-甲基-吡唑-4-甲腈 在 水 、 sodium hydroxide 作用下， 生成 5-氨基-1-甲基吡唑-4-甲酸
  参考文献：
  名称：

  PF-04859989作为基于结构的药物设计的模板：鉴定具有改善的亲脂性效率的新型吡唑系列不可逆KAT II抑制剂

  摘要：

  本文描述了新的吡唑系列不可逆KAT II抑制剂的基于结构的设计，合成和生物学评估。从二氢喹啉酮核心到四氢吡唑并吡啶并酮核心的1和2抑制剂骨架的修饰导致发现了一系列新的有效KAT II抑制剂，这些抑制剂具有出色的理化性质。在这些新的吡唑类似物中，化合物20是最有效和亲脂性最强的化合物，其k inact / K i值为112,000 M -1  s -1，亲脂性效率（LipE）为8.53。X射线晶体结构为20 KAT II的使用证明了有助于实现这种非凡效能和结合效率的关键功能。

  DOI：

  10.1016/j.bmcl.2013.02.039

文献信息

• [EN] CEPHEM COMPOUNDS<br/>[FR] CEPHEMES
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2005027909A1

  公开（公告）日：2005-03-31

  The present invention relates to a compound of the formula [I]: wherein R1 is lower alkyl or hydroxy (lower) alkyl, and R2 is hydrogen or amino protecting group, or R1 and R2 are bonded together and form lower alkylene ; R3 is -A-R6 wherein A is bond, -NHCO-(CH2CO)n-, lower alkylene, -NH-CO-CO- or the like, and R6 is (a) ou (b) wherein R7, R8, R9 and R10 are independently amino, guanidino, amidino or the like ; R4 is carboxy or protected carboxy; and R5 is amino or protected amino, or a pharmaceutically acceptable salt thereof, a process for preparing a compound of the formula [I], and a pharmaceutical composition comprising a compound of the formula [I] in admixture with a pharmaceutically acceptable carrier.

  本发明涉及一种公式的化合物[I]：其中R1是低级烷基或羟基（低级）烷基，R2是氢或氨基保护基团，或者R1和R2连接并形成低级亚烷基；R3是-A-R6，其中A是键，-NHCO-(CH2CO)n-，低级亚烷基，-NH-CO-CO-或类似物质，R6是(a)或(b)其中R7，R8，R9和R10是独立的氨基，胍基，脒基或类似物质；R4是羧基或受保护的羧基；R5是氨基或受保护的氨基，或药用可接受的盐，一种制备公式化合物[I]的方法，以及一种包括与药用可接受载体混合的公式化合物[I]的药物组合物。
• Development of a Selective Dual Discoidin Domain Receptor (DDR)/p38 Kinase Chemical Probe
  作者：Sandra Röhm、Benedict-Tilman Berger、Martin Schröder、Deep Chatterjee、Sebastian Mathea、Andreas C. Joerger、Daniel M. Pinkas、Joshua C. Bufton、Amelie Tjaden、Lohitesh Kovooru、Mark Kudolo、Christian Pohl、Alex N. Bullock、Susanne Müller、Stefan Laufer、Stefan Knapp

  DOI：10.1021/acs.jmedchem.1c00868

  日期：2021.9.23

  and various forms of cancer. Potent and selective inhibitors, so-called chemical probe compounds, have been developed to study DDR1/2 kinase signaling. However, these inhibitors showed undesired activity on other kinases such as the tyrosine protein kinase receptor TIE or tropomyosin receptor kinases, which are related to angiogenesis and neuronal toxicity. In this study, we optimized our recently published

  盘状蛋白结构域受体 1 和 2 (DDR1/2) 在纤维化疾病中发挥核心作用，例如肾和肺纤维化、动脉粥样硬化和各种形式的癌症。已开发出强效和选择性抑制剂，即所谓的化学探针化合物，用于研究 DDR1/2 激酶信号。然而，这些抑制剂对其他激酶（如酪氨酸蛋白激酶受体 TIE 或原肌球蛋白受体激酶）显示出不希望有的活性，这些激酶与血管生成和神经元毒性有关。在这项研究中，我们优化了我们最近发表的 p38 丝裂原活化蛋白激酶抑制剂7朝着有效的细胞活性双 DDR/p38 化学探针发展，并开发了一种结构相关的阴性对照。使用的结构引导设计方法提供了对 p38 的 P 环折叠过程以及非保守氨基酸的靶向如何调节抑制剂选择性的见解。开发和全面表征的 DDR/p38 探针30 (SR-302) 是研究 DDR 激酶在正常生理学和疾病发展中的作用的宝贵工具。
• [EN] SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES BICYCLIQUES SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE NADPH OXYDASE
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2018203298A1

  公开（公告）日：2018-11-08

  The present application relates to substituted fused heteroaryl and heterocyclic compounds, useful as nicotinamide adenine dinucleotide phosphate oxidase inhibitors (NADPH oxidase inhibitors), processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by NADPH oxidase. (Formula I)

  本申请涉及取代的融合杂环芳基和杂环化合物，用作烟酰胺腺嘌呤二核苷酸磷酸酶抑制剂（NADPH氧化酶抑制剂），其制备方法，包含这些化合物的药物组合物，以及这些化合物或组合物在治疗或预防由NADPH氧化酶介导的各种疾病、症状和/或障碍中的用途。 (分子式I)
• Novel Pyrazole-Hydrazone Derivatives Containing an Isoxazole Moiety: Design, Synthesis, and Antiviral Activity
  作者：Zaibo Yang、Pei Li、Xiuhai Gan

  DOI：10.3390/molecules23071798

  日期：——

  this study, a series of novel pyrazole-hydrazone derivatives containing an isoxazole moiety were synthesized. Antiviral bioassays indicated that some of the title compounds exhibited better in vivo antiviral activities against tobacco mosaic virus (TMV). In particular, compounds 6a, 6c and 6q exhibited the best curative activity, protection activity, and inactivation activity against TMV, respectively

  在这项研究中，合成了一系列含有异恶唑部分的新型吡唑-衍生物。抗病毒生物测定表明，某些标题化合物对烟草花叶病毒（TMV）表现出更好的体内抗病毒活性。特别地，化合物6a，6c和6q分别表现出对TMV的最佳治愈活性，保护活性和失活活性，优于宁南霉素。这项研究表明，这一系列含有异恶唑酰胺部分的新型吡唑-衍生物可以有效地控制TMV。
• 一种吡唑并嘧啶酮类化合物及其制备方法和 应用
  申请人：南开大学

  公开号：CN110066282B

  公开（公告）日：2020-07-10

  本发明属于除草剂技术领域，尤其涉及一种吡唑并嘧啶酮类化合物及其制备方法和应用。本发明提供的吡唑并嘧啶酮类化合物在1500克/公顷的剂量下，对四种供试植物(油菜、苋菜、稗草和马唐)均表现出很好的除草活性，且化合物4和化合物7对四种供试植物(油菜、苋菜、稗草和马唐)表现出将近100％的抑制率；同时，对化合物4和7进行减量除草活性测试，化合物7在93.75克/公顷时，仍然表现出很好的除草活性，具有非常好的应用前景。

表征谱图