6-溴喹唑啉-2,4-二酮 | 88145-89-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 6-溴喹唑啉-2,4-二酮
• 中文别名: 6-溴-2,4(1H,3H)-喹唑啉二酮；6-溴喹唑啉-2.4-二酮；六溴喹唑啉-2,4(1H,3H)-二酮
• 英文名称: 6-bromo-1H-quinazoline-2,4-dione
• 英文别名: 6-bromoquinazoline-2,4(1H,3H)-dione；6-bromoquinazoline-2,4-dione
• CAS: 88145-89-5
• 化学式: C₈H₅BrN₂O₂
• 分子量: 241.044
• InChiKey: JZDVFUAHGLJVQG-UHFFFAOYSA-N

物化性质

• 熔点：
  >300
• 密度：
  1.752±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi,Xn
• 危险类别码：
  R22
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温和干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
6-Bromoquinazoline-2,4(1H,3H)-dione
Product Name:
Synonyms: 6-Bromoquinazoline-2,4-diol

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
6-Bromoquinazoline-2,4(1H,3H)-dione
Ingredient name:
CAS number: 88145-89-5

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H5BrN2O2
Molecular weight: 241.0

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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

用途

6-溴喹唑啉-2,4-二酮（中文别名：六溴喹唑啉-2,4(1H,3H)-二酮）是常见的喹唑啉-2,4-酮衍生物。

基本信息

喹唑啉酮类化合物是一类含有嘧啶杂环的重要有机化合物。由于其结构简单，易于修饰改造，成为精细化工和医药合成中的重要中间体，广泛应用于抗菌、消炎、抗高血压、抗惊厥以及抗肿瘤药物中。6-取代-2,4-喹唑啉二酮衍生物具有优良的生物活性，在农药及医药领域有着广泛应用，如杀菌、除草、杀虫以及抗惊厥和神经保护等方面。

制备方法

以邻氨基溴代苯甲酸为起始原料，与氰酸钾反应，可以采用“一锅法”合成6-溴喹唑啉-2,4-二酮目标化合物[1]。该过程的反应式如下：

图 1：6-溴喹唑啉-2,4-二酮合成反应式

主要仪器与试剂 实验设备

• 电子分析天平
• 温度计
• 磁力搅拌器
• KDM 型控温电热套
• 铁架台及夹子
• 圆底烧瓶
• 抽滤漏斗
• 球形冷凝管
• 烧杯
• 真空干燥箱
• 循环水式真空泵
• 旋转蒸发仪

实验试剂

• 2-氨基-5-溴苯甲酸
• 氰酸钾
• 冰醋酸
• 氢氧化钠
• 浓盐酸等，均为分析纯

反应信息

• 作为反应物：
  描述：

  6-溴喹唑啉-2,4-二酮 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 反应 5.0h， 以75%的产率得到6-溴-2,4-二氯喹唑啉
  参考文献：
  名称：

  具有改善的大鼠NPR-A活性的新型人利钠肽受体A（NPR-A）激动剂的发现和体内效应

  摘要：

  通过优化喹唑啉衍生物的结构以改善对大鼠NPR-A的激动活性，评估了利钠肽受体A（NPR-A）激动剂的体内作用。发现在喹唑啉环上的4-位的1，4-顺式-氨基环己基脲部分和在2-位的d-丙氨醇的羟基是改善大鼠NPR-A活性的重要因素。我们确定了针对大鼠NPR-A的强效喹唑啉和吡啶并[2,3- d ]嘧啶衍生物，其纳摩尔浓度EC 50为两位数。该体内结果显示，化合物56b的以1.0 mg / kg / min的剂量给药可显着增加大鼠血浆cGMP浓度和尿量。我们发现了新型有效的NPR-A激动剂，其激动作用类似于心钠素。

  DOI：

  10.1016/j.bmc.2017.11.006
• 作为产物：
  描述：

  6-溴-2-硫代-2,3-二氢喹唑啉-4-酮 在 硫酸 作用下， 以 二甲基亚砜 为溶剂， 生成 6-溴喹唑啉-2,4-二酮
  参考文献：
  名称：

  Oxidative cyclocondensation of cyclic thio(seleno)ureas. 4. Electronic effects of the substituents and the medium

  摘要：

  DOI：

  10.1007/s10593-006-0123-1

文献信息

• FLAP MODULATORS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：US20150259357A1

  公开（公告）日：2015-09-17

  The present invention relates to compounds of Formula (I), or a form thereof, wherein ring A, R 1 , R 2 , R 3 , R 3 ′, L, W, and V are as defined herein, useful as FLAP modulators. The invention also relates to pharmaceutical compositions comprising compounds of Formula (I). Methods of making and using the compounds of Formula (I) are also within the scope of the invention

  本发明涉及式（I）的化合物，或其形式，其中环A，R1，R2，R3，R3'，L，W和V如本文所定义，可用作FLAP调节剂。该发明还涉及包含式（I）化合物的药物组合物。制备和使用式（I）化合物的方法也属于本发明的范围。
• 一种制备 2,4-（1H, 3H）-喹唑啉二酮类化合物的方法
  申请人：浙江外国语学院

  公开号：CN112778219A

  公开（公告）日：2021-05-11

  本发明公开了一种制备2,4‑（1H,3H）‑喹唑啉二酮类化合物的方法，它以式（1）所示的2‑氨基苯甲氰类化合物和二氧化碳为原料，在2‑羟基吡啶型离子液体中反应得到式（II）所示的2,4‑（1H,3H）‑喹唑啉二酮类化合物，其反应式如下：。本发明的离子液体在应用于制备2,4‑（1H,3H）‑喹唑啉二酮类化合物的反应中时，反应条件较为温和，产物的分离纯化过程较为简单，产物产率高，底物适用范围广。
• [EN] FACTOR XIa INHIBITORS<br/>[FR] INHIBITEURS DU FACTEUR XIA
  申请人：MERCK SHARP & DOHME

  公开号：WO2015164308A1

  公开（公告）日：2015-10-29

  The present invention provides a compound of Formula (I) and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XIa inhibitors or dual inhibitors of Factor XIa and plasma kallikrein.

  本发明提供了一种化合物(I)及包含一种或多种所述化合物的药物组合物，以及使用所述化合物用于治疗或预防血栓、栓塞、高凝血性或纤维变化的方法。这些化合物是选择性因子XIa抑制剂或因子XIa和血浆激肽原的双重抑制剂。
• 一种2,4-（1H，3H）-喹唑啉二酮及其衍生物的合成方法
  申请人：南京工业大学

  公开号：CN111454222B

  公开（公告）日：2023-05-23

  本发明公开了一种2,4‑(1H，3H)‑喹唑啉二酮及其衍生物的合成方法，采用CO2及氨基苄腈类化合物为原料，采用本发明所提出的式I的催化剂反应得到2,4‑(1H，3H)‑喹唑啉二酮及其衍生物。该方法所用试剂廉价易得，且为一步法即可合成产物，不需要高压高温的苛刻条件，整个反应体系中没有金属残留，所使用的催化剂还可以回收利用。
• Small Molecule Inhibitors of Toll-Like Receptor 9
  申请人：Lipford Grayson B.

  公开号：US20100160314A1

  公开（公告）日：2010-06-24

  Small molecule compounds and compositions containing said compounds useful for inhibiting signaling by certain Toll-like receptors (TLRs), particularly TLR9, are provided. The compounds and compositions can be used to inhibit immune responses, including unwanted immune responses in particular. Compounds, compositions, and methods are provided to treat a variety of conditions involving unwanted immune responses, including for example autoimmune disease, inflammation, transplant rejection, and sepsis.

  提供小分子化合物和包含所述化合物的组合物，用于抑制某些Toll样受体（TLRs）的信号传导，特别是TLR9。这些化合物和组合物可用于抑制免疫反应，包括特别是非所需的免疫反应。提供的化合物、组合物和方法可用于治疗涉及非所需免疫反应的各种病症，例如自身免疫病、炎症、移植排斥和败血症。