5-甲基胞嘧啶 | 554-01-8

• 物质功能分类: 生物化工 - 核苷类药物 - 核苷酸及其类似物
• 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: 5-甲基胞嘧啶
• 中文别名: 4-氨基-2-羟基-5-甲基嘧啶；5-甲基胞嗪；T55-甲基胞嘧啶
• 英文名称: 5-methylcytosin
• 英文别名: 5-methylcytosine；4-amino-5-methylpyrimidin-2-ol
• CAS: 554-01-8
• 化学式: C₅H₇N₃O
• mdl: MFCD00233537
• 分子量: 125.13
• InChiKey: LRSASMSXMSNRBT-UHFFFAOYSA-N

物化性质

• 熔点：
  270°C (rough estimate)
• 沸点：
  232.57°C (rough estimate)
• 密度：
  1.2602 (rough estimate)
• 溶解度：
  加热时少量溶于甲醇
• 物理描述：
  Solid
• 碰撞截面：
  121 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
• 稳定性/保质期：

  一、基本性质

  水中析出者含有1/2分子结晶水，最大吸收波长（pH2）为210nm和283nm。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• RTECS号：
  UW7362350
• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  二、贮存 应密封于阴凉干燥处保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Methylcytosine
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-Methylcytosine
CAS number: 554-01-8

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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.
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: C5H7N3O
Molecular weight: 125.1

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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

制备方法与用途

生物活性

5-甲基胞嘧啶是DNA碱基胞嘧啶的甲基化形式，作为哺乳动物核DNA中主要的表观遗传学标记，可能参与基因转录调控。

靶点

Human 内源性代谢物

| Human Endogenous Metabolite |

反应信息

• 作为反应物：
  描述：

  5-甲基胞嘧啶 在 4-phenylnaphthalene-1,2-dione 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 48.0h， 以71%的产率得到胸腺嘧啶
  参考文献：
  名称：

  邻萘醌催化好氧氧化策略的仿生氧化脱氨催化

  摘要：

  已经开发了一种邻萘醌催化的氧化脱氨反应，其中分子氧和水充当唯一的氧化剂和亲核试剂。当前的有氧脱氨反应是通过邻萘醌和胺之间的酮亚胺形成，随后质子重排和被水水解而进行的，这代表了人体中胺类被肝脏和肾脏的仿生氧化脱氨作用。邻位的相容性-萘醌与分子氧和水的有机催化剂开辟了一种新型的仿生催化剂体系，该体系可以用作多种含胺分子（如氨基酸和DNA核碱基）的多功能脱氨基胺。

  DOI：

  10.1021/acscatal.8b00992
• 作为产物：
  描述：

  2-ethylsulfanyl-5-methyl-pyrimidin-4-ylamine 生成 5-甲基胞嘧啶
  参考文献：
  名称：

  Harkins; Johnson, Journal of the American Chemical Society, 1929, vol. 51, p. 1241

  摘要：

  DOI：

文献信息

• Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators or caspases and inducers of apoptosis and the use thereof
  申请人：Cytovia, Inc.

  公开号：US20030069239A1

  公开（公告）日：2003-04-10

  The present invention is directed to substituted 2-aryl-4-arylaminopyrimidine and analogs thereof, represented by the general Formula I: 1 wherein A, Ar 1 , Ar 2 , R 1 and R 3 are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. The compounds of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及被一般式I所代表的取代的2-芳基-4-芳基氨基嘧啶及其类似物： 其中A，Ar1，Ar2，R1和R3在此处被定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。本发明的化合物可用于诱导在出现未受控制的异常细胞生长和扩散的各种临床病况中的细胞死亡。
• CROSSLINKED ARTIFICIAL NUCLEIC ACID ALNA
  申请人：MITSUBISHI TANABE PHARMA CORPORATION

  公开号：US20220002336A1

  公开（公告）日：2022-01-06

  The present invention provides a novel bridged artificial nucleic acid and an oligomer containing the same as a monomer. The present invention provides specifically a compound represented by general formula (I) (wherein each symbol is the same as defined in the specification) or salts thereof; as well as an oligonucleotide compound represented by general formula (I′) (wherein each symbol is the same as defined in the specification) or salts thereof.

  本发明提供了一种新型的桥接人工核酸和含有该人工核酸作为单体的寡聚物。本发明具体提供了一种由通式（I）表示的化合物（其中每个符号与规范中定义的相同）或其盐；以及由通式（I'）表示的寡核苷酸化合物（其中每个符号与规范中定义的相同）或其盐。
• Nucleic acid derived allenols. Unusual analogs of nucleosides with antiretroviral activity
  作者：Shashikant Phadtare、Jiri Zemlicka

  DOI：10.1021/ja00197a063

  日期：1989.7

  L'alkylation de plusieurs bases puriques ou pyrimidiques par des chloro butynes-2 ou des butyne-2ols fournit les bases substituees correspondantes. Une cyclisation en milieu basique se produit et l'on obtient les composes dihydro-2,5 furyl-2-B (ou B=guanine, cytosine, adenine). L'activite biologique de ces composes est etudiee

  L'烷基化加氢碱基puriques ou pyrimidiques par des chloro butynes-2 ou des butyne-2ols Fournit les bases substitueesrespondantes。Une cyclisation en milieu basique se produit et l'on obtient les 组成 dihydro-2,5 furyl-2-B（ou B = 鸟嘌呤、胞嘧啶、腺嘌呤）。L'activite biologique de ces composes est etudiee
• HETEROCYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20210087186A1

  公开（公告）日：2021-03-25

  The present invention provides a compound having a glucosylceramide lowering action (e.g., promoting glucosylceramide metabolism, inhibition of glucosylceramide synthesis, promoting glucosylceramide catabolism, etc.), which is expected to be useful as an agent for the prophylaxis or treatment of lysosome diseases (e.g., Gaucher's disease), neurodegenerative diseases (e.g., Parkinson's disease, Lewy body dementia, multiple-system atrophy) and the like. The present invention relates to a compound represented by the formula (I) wherein each symbol is as described in the specification, or a salt thereof.

  本发明提供一种具有降低葡糖鞘脂的作用（例如促进葡糖鞘脂代谢、抑制葡糖鞘脂合成、促进葡糖鞘脂分解等）的化合物，预计可用作预防或治疗溶酶体疾病（例如高雪氏病）、神经退行性疾病（例如帕金森病、路易体痴呆症、多系统萎缩症）等的药剂。本发明涉及一种由式（I）表示的化合物 其中每个符号如说明书中所述，或其盐。
• Preliminary SAR and biological evaluation of potent HIV-1 protease inhibitors with pyrimidine bases as novel P2 ligands to enhance activity against DRV-resistant HIV-1 variants
  作者：Mei Zhu、Ling Ma、Huiyu Zhou、Biao Dong、Yujia Wang、Zhen Wang、Jinming Zhou、Guoning Zhang、Juxian Wang、Chen Liang、Shan Cen、Yucheng Wang

  DOI：10.1016/j.ejmech.2019.111866

  日期：2020.1

  to P2 ligands might enhance the potency of Human Immunodeficiency Virus-1 (HIV-1) protease inhibitors because of the carbonyl and amino groups promoting the formation of extensive hydrogen bonding interactions. In this work, we provide evidence that inhibitor 10e, with N-2-(2,4-Dioxo-3,4-dihydropyrimidin-1(2H)-yl) acetamide as the P2 ligand and a 4-methoxylphenylsulfonamide as the P2' ligand, displayed

  将嘧啶碱基（核酸的基本成分）引入P2配体可能会增强人类免疫缺陷病毒1（HIV-1）蛋白酶抑制剂的效力，因为羰基和氨基会促进广泛的氢键相互作用的形成。在这项工作中，我们提供的证据是抑制剂10e，以N-2-（2,4-二氧代-3,4-二氢嘧啶-1（2H）-基）乙酰胺为P2配体，以4-甲氧基苯基磺酰胺为P2'配体具有显着的酶抑制和抗病毒活性，体外IC50为2.53 nM，体内对野生型HIV-1的抑制率为68％，细胞毒性低。该抑制剂还对DRV耐药的HIV-1变体表现出明显的抗病毒活性，这对进一步研究具有重要的价值。

表征谱图