2-肼基-6-甲基嘧啶-4-醇 | 37893-08-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 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-肼基-6-甲基嘧啶-4-醇
• 中文别名: 6-甲基-2,4(1h,3H-)-嘧啶二酮-2-肼酮(9ci)
• 英文名称: 2-hydrazino-6-methylpyrimidin-4(3H)-one
• 英文别名: 2-hydrazinyl-6-methylpyrimidin-4(3H)-one；2-hydrazinyl-6-methylpyrimidin-4-one；2-hydrazineyl-6-methylpyrimidin-4(3H)-one；2-Hydrazino-6-methylpyrimidin-4-ol；2-hydrazinyl-4-methyl-1H-pyrimidin-6-one
• CAS: 37893-08-6
• 化学式: C₅H₈N₄O
• mdl: MFCD00205260
• 分子量: 140.145
• InChiKey: RFKCQKWRFAJRPY-UHFFFAOYSA-N

物化性质

• 熔点：
  242-244 °C
• 密度：
  1.52±0.1 g/cm3(Predicted)
• 溶解度：
  13.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 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：
  79.5
• 氢给体数：
  3
• 氢受体数：
  3

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: 2-Hydrazino-6-methylpyrimidin-4-ol
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: 2-Hydrazino-6-methylpyrimidin-4-ol
CAS number: 37893-08-6

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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, under −20◦C.
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: C5H8N4O
Molecular weight: 140.1

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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-肼基-6-甲基嘧啶-4-醇 在 盐酸 作用下， 生成 6-甲基尿嘧啶
  参考文献：
  名称：

  Sirakawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 635,638

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基硫脲嘧啶 在 一水合肼 、 三乙胺 作用下， 以 异丙醇 、 丙酮 为溶剂， 反应 0.25h， 生成 2-肼基-6-甲基嘧啶-4-醇
  参考文献：
  名称：

  基于结构的设计和嘧啶和1,2,4-三唑并[4,3-a]嘧啶类基质金属蛋白酶-10/13抑制剂通过Dimroth重排向目标多药理学优化。

  摘要：

  最近，随着人们对基质金属蛋白酶（MMPs）-10和-13在基质金属蛋白酶（MMPs）网络中的相关性及其对多种疾病（如关节炎，癌症，动脉粥样硬化和阿尔茨海默氏病）的抑制作用的认识不断增强，人们对基质金属蛋白酶（MMPs）-10和-13的兴趣日益浓厚。在这种方法中，双重MMP-10 / 13抑制被公开为靶向多药理学的新方法。尽管已知几种有效的MMP-13抑制剂，但报道的有效和选择性MMP-10抑制剂很少。这项研究描述了新型MMP-10 / 13抑制剂的设计，合成和优化，这些抑制剂具有增强的MMP-10效力和对多药理学的选择性。从对MMP-10抑制作用较弱的基于铅融合的嘧啶的MMP-13抑制剂开始，合理设计了基于嘧啶和嘧啶融合支架的结构，以增强与MMP-13平行的抗MMP-10活性。首先，通过常规和超声辅助方法合成了一系列6-甲基嘧啶-4-酮6-10，然后评估了其对MMP-10 / 13的抑制作

  DOI：

  10.1016/j.bioorg.2020.103616

文献信息

• [EN] NOVEL ANTIPARASITIC COMPOUNDS AND METHODS<br/>[FR] NOUVEAUX COMPOSÉS ANTIPARASITAIRES ET PROCÉDÉS
  申请人：UNIV TEXAS

  公开号：WO2021077102A1

  公开（公告）日：2021-04-22

  Novel compounds for treating or inhibiting leishmaniasis and other parasitic protozoan diseases are disclosed herein. The compounds bind to Leishmania tubulin, induce parasite microtubule polymerization, stall Leishmania cell division, and have broad antiparasitic activity.

  本发明公开了用于治疗或抑制利什曼病和其他寄生原虫疾病的新型化合物。这些化合物能够结合到利什曼原虫的微管蛋白，诱导寄生虫微管聚合，阻碍利什曼细胞分裂，并且具有广泛的抗寄生虫活性。
• [EN] HETEROARYL DERIVATIVES AS SEPIAPTERIN REDUCTASE INHIBITORS<br/>[FR] DÉRIVÉS D'HÉTÉROARYLE À UTILISER EN TANT QU'INHIBITEURS DE SÉPIAPTÉRINE RÉDUCTASE
  申请人：QUARTET MEDICINE INC

  公开号：WO2017059191A1

  公开（公告）日：2017-04-06

  Inhibitors of sepiapterin reductase of formula (I) or (I'), wherein the substituents are defined as in the claims, and uses of sepiapterin reductase inhibitors in analgesia, treatment of acute and chronic pain, anti-inflammation, and immune cell regulation are disclosed.

  式(I)或(I')的色氨酰还原酶抑制剂，其中取代基如权利要求中所定义，以及这些色氨酰还原酶抑制剂在镇痛、治疗急慢性疼痛、抗炎和免疫细胞调节中的用途被公开。
• Synthesis of novel N- and C-acyclic nucleosides derived from 2-hydrazino-6-methyluracil
  作者：hayam Abdelsalaam、Alaa El_din Gafaar

  DOI：10.21608/ejchem.2020.21459.2279

  日期：2020.1.15

  The reaction of 2-hydrazino-6-methyl uracil with different aldo- sugars yields the corresponding N-acyclic glycosides. However, some of them have cyclized successfully to form a new fused triazole ring. Apparently, such cyclization depends upon the Stereochemistry of the N-glycoside intermediates that produce the C-glycosides.”

  2-肼基-6-甲基尿嘧啶与不同的醛糖的反应产生相应的N-无环糖苷。但是，其中一些已成功环化形成新的稠合三唑环。显然，这种环化取决于产生C-糖苷的N-糖苷中间体的立体化学。”
• Pyrazolyl-pyrimidones inhibit the function of human solute carrier protein SLC11A2 (hDMT1) by metal chelation
  作者：Marion Poirier、Jonai Pujol-Giménez、Cristina Manatschal、Sven Bühlmann、Ahmed Embaby、Sacha Javor、Matthias A. Hediger、Jean-Louis Reymond

  DOI：10.1039/d0md00085j

  日期：——

  Solute carrier proteins (SLCs) control fluxes of ions and molecules across biological membranes and represent an emerging class of drug targets. SLC11A2 (hDMT1) mediates intestinal iron uptake and its inhibition might be used to treat iron overload diseases such as hereditary hemochromatosis. Here we report a micromolar (IC50 = 1.1 μM) pyrazolyl-pyrimidone inhibitor of radiolabeled iron uptake in hDMT1

  溶质载体蛋白（SLC）控制离子和分子穿过生物膜的通量，代表了新兴的一类药物靶标。SLC11A2（hDMT1）介导肠道铁的吸收，其抑制作用可能用于治疗铁超负荷疾病，例如遗传性血色素沉着病。在这里我们报告了微摩尔（IC 50= 1.1μM）通过非竞争机制作用的过表达hDMT1的HEK293细胞中放射性标记铁摄取的吡唑基-嘧啶酮抑制剂，但不影响转运蛋白的电生理特性。等温滴定量热法，与钙黄绿素的竞争，放射性铁的诱导沉淀以及无关铁转运蛋白SLC39A8（hZIP8）的交叉抑制表明抑制作用是由金属螯合介导的。在ChEMBL中绘制成千上万的吡唑并嘧啶酮和类似的2,2'-二氮杂双芳基的化学空间图表明，其报道的活性可能部分反映了金属螯合。泛分析干扰化合物（PAINS）中未列出此类金属螯合基团，但在处理SLC时应进行检查。
• Antitubercular 2-Pyrazolylpyrimidinones: Structure–Activity Relationship and Mode-of-Action Studies
  作者：Candice Soares de Melo、Vinayak Singh、Alissa Myrick、Sandile B. Simelane、Dale Taylor、Christel Brunschwig、Nina Lawrence、Dirk Schnappinger、Curtis A. Engelhart、Anuradha Kumar、Tanya Parish、Qin Su、Timothy G. Myers、Helena I. M. Boshoff、Clifton E. Barry、Frederick A. Sirgel、Paul D. van Helden、Kirsteen I. Buchanan、Tracy Bayliss、Simon R. Green、Peter C. Ray、Paul G. Wyatt、Gregory S. Basarab、Charles J. Eyermann、Kelly Chibale、Sandeep R. Ghorpade

  DOI：10.1021/acs.jmedchem.0c01727

  日期：2021.1.14

  transcriptional profiling and the checkerboard board 2D-MIC assay in the presence of varying concentrations of ferrous salt indicated perturbation of the Fe-homeostasis by the compounds. Structure–activity relationship studies identified potent compounds with good physicochemical properties and in vitro microsomal metabolic stability with moderate selectivity over cytotoxicity against mammalian cell lines

  对 Medicines for Malaria Venture 的抗结核分枝杆菌( Mtb )化合物库进行表型筛选，鉴定出一组具有泛活性的 2-吡唑基嘧啶酮。使用不同的结核分枝杆菌工具菌株对这些活性物质进行生物学分类，提出了一种新的作用机制。这些化合物对复制的Mtb具有杀菌作用，并保留了对Mtb临床分离株的效力。尽管选定的Mtb MmpL3 突变株表现出对这些化合物的耐药性，但针对 mmpL3 亚型的最低抑制浓度 (MIC) 没有变化，表明 MmpL3 突变是这些化合物的可能耐药机制，但不一定是靶点。在不同浓度的亚铁盐存在下，RNA 转录谱和棋盘 2D-MIC 测定表明这些化合物对 Fe 稳态的扰动。结构-活性关系研究确定了具有良好理化性质和体外微粒体代谢稳定性的有效化合物，对哺乳动物细胞系的细胞毒性具有中等选择性。