5-溴-6-氮尿嘧啶 | 4956-05-2

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 中文名称: 5-溴-6-氮尿嘧啶
• 中文别名: 5-溴-6-氮杂尿嘧啶；6-溴-1,2,4-三嗪-3,5(2H,4H)-二酮
• 英文名称: 6-bromo-1,2,4-triazine-3,5(2H,4H)-dione
• 英文别名: 5-bromo-6-azauracil；6-bromo-2H-1,2,4-triazine-3,5-dione；6-bromo-2,4-dihydro-1,2,4-triazine-3,5-dione
• CAS: 4956-05-2
• 化学式: C₃H₂BrN₃O₂
• mdl: MFCD00128423
• 分子量: 191.972
• InChiKey: VNTFEWXYAOATFA-UHFFFAOYSA-N

物化性质

• 熔点：
  232-234 °C
• 密度：
  2.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933699090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-6-azauracil
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-Bromo-6-azauracil
CAS number: 4956-05-2

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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: C3H2BrN3O2
Molecular weight: 192

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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, hydrogen bromide.

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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

制备方法

医药生物化工中间体。

用途简介

暂无相关信息。

反应信息

• 作为反应物：
  描述：

  5-溴-6-氮尿嘧啶 在 盐酸 作用下， 以 水 为溶剂， 以90 %的产率得到6-chloro-2H-[1,2,4]triazine-3,5-dione
  参考文献：
  名称：

  一种3,5,6-三氯-[1,2,4]-噻嗪的合成方法

  摘要：

  本发明公开了一种3,5,6‑三氯‑[1,2,4]‑噻嗪的合成方法，包括如下步骤：S1、6‑氮杂尿嘧啶和液溴在60℃‑70℃下反应生成5‑溴‑6‑氮尿嘧啶；S2、5‑溴‑6‑氮尿嘧啶和浓盐酸在100℃‑105℃下反应生成5‑氯‑6‑氮尿嘧啶；S3、5‑氯‑6‑氮尿嘧啶与三氯氧磷在常温下反应生成3,5,6‑三氯‑[1,2,4]‑噻嗪。本发明3,5,6‑三氯‑[1,2,4]‑噻嗪的合成方法，合成方法简单，反应条件温和，过程可控，便于工业化生产。

  公开号：

  CN117658936A
• 作为产物：
  描述：

  6-氮杂脲嘧啶 在 水 、 溴 作用下， 反应 27.0h， 以82%的产率得到5-溴-6-氮尿嘧啶
  参考文献：
  名称：

  Synthesis of C-ribosyl imidazo[2,1-f  ][1,2,4]triazines as inhibitors of adenosine and AMP deaminases

  摘要：

  新咪唑并[2,1-f][1,2,4]三嗪 27 的 3-β-D-ribofuranoside 6 与核苷脱氨基福尔马林 1 是同分异构体和等电子体，后者是腺苷脱氨酶 (ADA) 的良好抑制剂，而其 5′-monophosphate 2 则是腺苷 5′-monophosphate deaminase (AMPDA) 的良好抑制剂。6 的 6-甲硫基衍生物 7 是通过单环 1,2,4-三嗪 9 与溴醛 10 缩合合成的，缩合过程伴随着环化反应，从而得到受保护的 C 核苷 21；21 的 8-甲硫基通过肼置换和氧化作用去除。1,2,4-三嗪 9 与氯乙醛或其二甲基缩醛发生类似的环化反应，得到 6,8-双（甲硫基）咪唑并[2,1-f][1,2,4]三嗪 17，通过两种途径转化为母杂环 27，以及新环系统的单取代和二取代衍生物（19、20、24、25、28-30）。核苷 7 是哺乳动物 ADA 的抑制剂（IC50 40 µM）。

  DOI：

  10.1039/a904065j
• 作为试剂：
  描述：

  溴 、 6-氮杂脲嘧啶 在 水 、 5-溴-6-氮尿嘧啶 作用下， 以 水 为溶剂， 反应 26.0h， 以affording the title compound 6-bromo-1,2,4-triazine-3,5(2H,4H)-dione (1.97 g, 10.26 mmol, 46.4% yield) as a white crystalline solid的产率得到5-溴-6-氮尿嘧啶
  参考文献：
  名称：

  Azabicyclo [3. 1. 0] hexyl derivatives as modulators of dopamine D3 receptors

  摘要：

  本发明涉及公式（I）或其盐的新化合物： 其中， G选择自：苯基、5-或6-成员单环杂芳基团或8-至11-成员杂芳双环基团； p为0至5的整数； R1为卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R6基团；当p为2至5的整数时，每个R1可以相同或不同； R2为氢或C1-4烷基； n为3、4、5或6； R6为选择自：异噁唑基、—CH2—N-吡咯基、1,1-二氧化-2-异噻唑烷基、噻唑基、吡啶基、2-吡咯烷基的基团，并且该R6基团可选地由1或2个取自卤素、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基和C1-4酰基的取代基取代； R4选择自：氢、卤素、羟基、氰基、C1-4烷基、C3-7环烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和NR′R″；或R4为苯基、5-14成员杂环基；任何此类苯基或杂环基均可选择性地由1、2、3或4个取自卤素、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、C1-4酰基、卤代C1-4烷氧基和SF5的取代基取代； R7为氢或C1-2烷基； R′为H、C1-4烷基或C1-4酰基； R″定义为R′； R′和R″与相互连接的氮原子一起可以形成5-、6-成员饱和或不饱和杂环环； 以及它们在治疗中的用途，作为多巴胺D3受体调节剂。

  公开号：

  US08217168B2

文献信息

• Discovery of 1,2,4-triazine-based derivatives as novel neddylation inhibitors and anticancer activity studies against gastric cancer MGC-803 cells
  作者：Jian Song、Xin-Xin Cui、Bo-Wen Wu、Dong Li、Sheng-Hui Wang、Lei Shi、Ting Zhu、Yan-Bing Zhang、Sai-Yang Zhang

  DOI：10.1016/j.bmcl.2019.126791

  日期：2020.1

  Neddylation modification is often over-expressed in a variety of human tumor cells. Therefore, targeting neddylation pathway may represent a potential approach to the treatment of human tumors. Herein, we describe the discovery of a hit scaffold from our in-house library and further structure-based optimizations. In this work, compound V11 could block the neddylation and inhibit the activity of NAE

  Neddylation修饰通常在多种人类肿瘤细胞中过表达。因此，靶向腺苷酸化途径可能代表了一种治疗人类肿瘤的潜在方法。在此，我们描述了从我们的内部库中发现命中支架的发现以及进一步基于结构的优化。在这项工作中，化合物V11可能会阻断糊化作用并抑制NAE的活性（EC50值为3.56 µM），并且还观察到Ubc12-NEDD8结合的剂量依赖性降低。分子对接结果表明，化合物V11可以通过氢键和疏水相互作用与NAE紧密结合。化合物V11对胃癌MGC-803细胞表现出最佳的抗增殖能力，IC50值为8.22μM。进一步的抗癌活性研究表明，化合物V11抑制了MGC-803细胞的生长，导致细胞周期停滞在G2 / M期，并通过外部和固有凋亡途径诱导凋亡。所有的发现表明1,2,4-三嗪支架可能为进一步开发联结抑制剂提供了一个新颖的支架，化合物V11可能是具有抗癌活性的潜在联结抑制剂。
• [EN] BICYCLIC COMPOUNDS<br/>[FR] COMPOSÉS BICYCLIQUES
  申请人：KALYRA PHARMACEUTICALS INC

  公开号：WO2016183094A1

  公开（公告）日：2016-11-17

  Disclosed herein are nitrogen-containing bicyclic compounds, together with pharmaceutical compositions and methods of ameliorating and/or treating a cancer described herein with one or more of the compounds described herein.

  本文披露了含氮的双环化合物，以及使用本文描述的一个或多个化合物改善和/或治疗本文描述的癌症的药物组合物和方法。
• [EN] AZABICYCLO [3. 1. 0] HEXYL DERIVATIVES AS MODULATORS OF DOPAMINE D3 RECEPTORS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXO GROUP LTD

  公开号：WO2009043884A1

  公开（公告）日：2009-04-09

  The present invention relates to novel compounds of formula (I) or a salt thereof, wherein G is selected from a group consisting of: phenyl, a 5- or 6-membered monocyclic heteroaryl group, or a 8- to 11-membered heteroaryl bicyclic group; p is an integer ranging from 0 to 5; R1 is halogen, hydroxy, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, C1-4alkanoyl and SF5; or corresponds to a group R6; and when p is an integer ranging from 2 to 5, each R1 may be the same or different; R2 is hydrogen or C1-4alkyl; n is 3, 4, 5 or 6; R6 is a moiety selected from the group consisting of: isoxazolyl, -CH2-N-pyrrolyl, 1,1-dioxido-2-isothiazolidinyl, thienyl, thiazolyl, pyridyl, 2-pyrrolidinonyl, and such R6 group is optionally substituted by one or two substituents selected from: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, C1-4alkanoyl; R4 is selected in the group consisting of: hydrogen, halogen, hydroxy, cyano, C1-4alkyl, C3-7 cycloalkyl, haloC1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, C1-4alkanoyl and NR'R'; or R4 is a phenyl group, a 5-14 membered heterocyclic group; and any of such phenyl or heterocyclic group is optionally substituted by 1, 2, 3 or 4 substituents selected from the group consisting of: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, C1-4alkanoyl, haloC1-4alkoxy and SF5; R7 is hydrogen or C1-2alkyl; R' is H, C1-4 alkyl or C1-4 alkanoyl; R' is defined as R'; R' and R' taken together with the interconnecting nitrogen atom may form a 5-, 6-membered saturated or unsaturated heterocyclic ring; processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as modulators of dopamine D3 receptors, e.g. to treat drug dependency, as antipsychotic agents, to treat obsessive compulsive spectrum disorders, or premature ejaculation.

  本发明涉及式(I)的新化合物或其盐，其中G选自以下组成的一组：苯基，5-或6-成员单环杂环基，或8-至11-成员杂环双环基；p是一个从0到5的整数；R1是卤素，羟基，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，卤代C1-4烷氧基，C1-4烷酰基和SF5；或对应于一个R6基团；当p是一个从2到5的整数时，每个R1可以相同也可以不同；R2是氢或C1-4烷基；n是3、4、5或6；R6是从以下组成的基团中选择的一个：异噁唑基，-CH2-N-吡咯基，1,1-二氧化-2-异噻唑啉基，噻吩基，噻唑基，吡啶基，2-吡咯烷基，以及这样的R6基团可以选择地被来自以下组成的一个或两个取代基取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4烷酰基；R4在以下组成的基团中选择：氢，卤素，羟基，氰基，C1-4烷基，C3-7环烷基，卤代C1-4烷基，C1-4烷氧基，卤代C1-4烷氧基，C1-4烷酰基和NR'R'；或R4是一个苯基，一个5-14成员杂环基；和任何这样的苯基或杂环基可以选择地被来自以下组成的1、2、3或4个取代基取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4烷酰基，卤代C1-4烷氧基和SF5；R7是氢或C1-2烷基；R'是H，C1-4烷基或C1-4烷酰基；R'被定义为R'；R'和R'连同相互连接的氮原子可以形成一个5-、6-成员饱和或不饱和杂环环；它们的制备方法，用于这些方法的中间体，含有它们的药物组合物以及它们在治疗中的用途，作为多巴胺D3受体调节剂，例如用于治疗药物依赖，作为抗精神病药物，用于治疗强迫症谱系障碍，或早泄。
• [EN] SUBSTITUTED TRIAZINONES AS THYROID HORMONE RECEPTOR AGONISTS<br/>[FR] TRIAZINONES SUBSTITUÉES EN TANT QU'AGONISTES DU RÉCEPTEUR DE L'HORMONE THYROÏDIENNE
  申请人：ECCOGENE SHANGHAI CO LTD

  公开号：WO2021143706A1

  公开（公告）日：2021-07-22

  The application relates to a compound of Formula (I') or (I), or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer, or tautomer thereof, which modulates the activity of thyroid hormone receptors, a pharmaceutical composition comprising a compound of Formula (I') or (I), and a method of treating or preventing a disease or disorder regulated by thyroid hormone.

  该申请涉及式(I')或(I)的化合物，或其药物可接受的盐、水合物、溶剂化物、前药、立体异构体或互变异构体，其可调节甲状腺激素受体的活性，包含式(I')或(I)的化合物的药物组合物，以及用于治疗或预防由甲状腺激素调节的疾病或失调的方法。
• 2,6-二取代的1,2,4-三嗪-3,5-二酮化合物及其制备方法和应用
  申请人：昆药集团股份有限公司

  公开号：CN113278013B

  公开（公告）日：2022-09-23

  本发明提供了一种2,6‑二取代的1,2,4‑三嗪‑3,5‑二酮化合物，具有式Ⅰ所示结构，或其药学上可接受的盐。上述三嗪酮衍生物结构新颖且显示出优良的THRβ激动作用，能够作为甲状腺激素受体相关疾病的治疗和/或预防药物来发挥作用。