6-溴-3-甲基喹唑啉-4(3H)-酮 | 57573-59-8

• 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-3-甲基喹唑啉-4(3H)-酮
• 英文名称: 6-bromo-3-methylquinazolin-4(3H)-one
• 英文别名: 6-bromo-3-methyl-quinazolin-4-one；6-bromo-3-methylquinazolin-4-one
• CAS: 57573-59-8
• 化学式: C₉H₇BrN₂O
• 分子量: 239.071
• InChiKey: MCSVSXROESVYLR-UHFFFAOYSA-N

物化性质

• 沸点：
  364.2±44.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromo-3-methylquinazolin-4(3H)-one
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: 6-Bromo-3-methylquinazolin-4(3H)-one
CAS number: 57573-59-8

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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: C9H7BrN2O
Molecular weight: 239.1

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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, 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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  6-溴-4-羟基喹唑啉	6-bromoquinazolin-4(3H)-one	32084-59-6	C8H5BrN2O	225.044

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  6-氨基-3-甲基喹唑啉-4(3H)-酮	6-amino-3-methylquinazolin-4-one	16064-23-6	C9H9N3O	175.19
  ——	3-methyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid	878756-93-5	C10H8N2O3	204.185
  ——	6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-methylquinazolin-4(3H)-one	1290634-38-6	C15H18N4O	270.334
  ——	3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-4(3H)-one	1209485-71-1	C15H19BN2O3	286.138
  ——	N-(6-(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)-1H-benzo[d]imidazole-2-yl)propionamide	——	C19H17N5O2	347.376
  ——	N-(4-methyl-3-(3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylamino)phenyl)propane-1-sulfonamide	1396311-01-5	C19H22N4O3S	386.475
  ——	tert-butyl (4-methyl-3-((3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)amino)phenyl)carbamate	878745-39-2	C21H24N4O3	380.447

反应信息

• 作为反应物：
  描述：

  6-溴-3-甲基喹唑啉-4(3H)-酮 在 bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) 、 双(二氧化硫)-1,4-二氮杂双环[2.2.2]辛烷加合物 、 三乙胺 、 N-氟代双苯磺酰胺 作用下， 以 异丙醇 为溶剂， 反应 27.0h， 以56%的产率得到
  参考文献：
  名称：

  一锅钯催化从芳基溴化物合成磺酰氟†

  摘要：

  描述了利用钯催化从芳基和杂芳基溴化物温和有效地合成磺酰氟的方法。该方法涉及使用DABSO作为SO 2源进行钯催化的芳基溴的磺化反应，然后进行原位反应。用亲电子氟源NFSI处理所得的亚磺酸盐。该序列代表了芳基溴化物磺酰化的第一种通用方法，并为先前描述的磺酰氟合成提供了实用的一锅替代品，从而可以快速使用这些生物学上重要的分子。证明了优异的官能团耐受性，并且成功地在多种活性药物成分及其前体上实现了转化。还证明了肽衍生的磺酰氟的制备。

  DOI：

  10.1039/c6sc03924c
• 作为产物：
  描述：

  靛红 在 N-溴代丁二酰亚胺(NBS) 、 aluminum potassium sulfate dodecahydrate 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 528.25h， 生成 6-溴-3-甲基喹唑啉-4(3H)-酮
  参考文献：
  名称：

  某些氨基和硫烷基-3 H-喹唑啉-4-酮衍生物的合成及生物学评价

  摘要：

  摘要在Buchwald–Hartwig型反应条件下，在Pd（OAc）2 / Xantphos体系存在下，通过6-溴喹唑啉酮与芳基或烷基胺和硫醇的反应，制备了一系列6-取代喹唑啉酮衍生物。通过5-溴氨基苯甲酸酐，原甲酸三乙酯和适当的胺的三组分反应获得6-溴喹唑啉酮。对合成化合物对HT29和HCT116细胞系以及对淋巴细胞的潜在细胞毒性的生物学筛选显示，喹唑啉酮的某些衍生物具有显着的抗癌活性。报告了详细的合成，光谱数据和生物学分析。 图形概要

  DOI：

  10.1007/s00706-015-1508-6

文献信息

• [EN] SUBSTITUTED IMIDAZOLES FOR THE INHIBITION OF TGF-BETA AND METHODS OF TREATMENT<br/>[FR] IMIDAZOLES SUBSTITUÉS POUR L'INHIBITION DE TGF-BÊTA ET MÉTHODES DE TRAITEMENT
  申请人：CLAVIUS PHARMACEUTICALS LLC

  公开号：WO2020041562A1

  公开（公告）日：2020-02-27

  This disclosure relates to low molecular weight substituted imidazoles that inhibit the TGF-b signaling pathway. More specifically, this disclosure relates to methods of using said imidazoles for the treatment of diseases related to the TGF-b signaling pathways including, but not limited to, atherosclerosis, Marfan syndrome, Loeys-Dietz syndrome, obesity, diabetes, multiple sclerosis, keratoconus, idiopathic pulmonary fibrosis, Alzheimer's Disease, chronic kidney disease, and scleroderma.

  这项披露涉及抑制TGF-b信号通路的低分子量取代咪唑化合物。更具体地，这项披露涉及使用上述咪唑化合物治疗与TGF-b信号通路相关的疾病的方法，包括但不限于动脉粥样硬化、马凡综合征、洛伊斯-迪茨综合征、肥胖症、糖尿病、多发性硬化、圆锥角膜、特发性肺纤维化、阿尔茨海默病、慢性肾病和硬皮病。
• [EN] CONDENSED AZINE - DERIVATIVES FOR THE TREATMENT OF DISEASES RELATED TO THE ACETYLCHOLINE RECEPTOR<br/>[FR] DÉRIVÉS CONDENSÉS D'AZINE POUR LE TRAITEMENT DE MALADIES LIÉES AUX RÉCEPTEURS DE L'ACÉTYLCHOLINE
  申请人：ORGANON NV

  公开号：WO2011045258A1

  公开（公告）日：2011-04-21

  The present invention relates to a heterocyclic derivative of formula (I) wherein the variables are as defined in the specification or to a pharmaceutically acceptable salt or solvate thereof. The present invention further relates to pharmaceutical compositions comprising said heterocyclic derivatives and to their use in therapy, for instance in the treatment or prevention of disorders mediated by nicotinic acetylcholine receptors, such as schizophrenia and Alzheimer's disease.

  本发明涉及式(I)的杂环衍生物，其中变量如规范中所定义，或其药用可接受盐或溶剂。本发明还涉及包含所述杂环衍生物的药物组合物，以及它们在治疗中的应用，例如在治疗或预防由尼古丁乙酰胆碱受体介导的疾病，如精神分裂症和阿尔茨海默病。
• Late-Stage <i>N</i>-Me Selective Arylation of Trialkylamines Enabled by Ni/Photoredox Dual Catalysis
  作者：Yangyang Shen、Tomislav Rovis

  DOI：10.1021/jacs.1c08157

  日期：2021.10.13

  The diversity and wide availability of trialkylamines render them ideal sources for rapid construction of complex amine architectures. Herein, we report that a nickel/photoredox dual catalysis strategy affects site-selective α-arylation of various trialkylamines. Our catalytic system shows exclusive N-Me selectivity with a wide range of trialkylamines under mild conditions, even in the context of late-stage

  三烷基胺的多样性和广泛可用性使其成为快速构建复杂胺结构的理想来源。在此，我们报道镍/光氧化还原双重催化策略影响各种三烷基胺的位点选择性α-芳基化。我们的催化系统在温和条件下对多种三烷基胺表现出独特的N -Me 选择性，即使是在带有这种共同结构基序的药物化合物的后期芳基化的情况下也是如此。机理研究表明镍催化剂在拦截α-氨基自由基时表现出非常规的行为，其中只有伯α-氨基自由基经历了成功的交叉偶联过程。
• Novel Quinazolinone Inhibitors of ALK2 Flip between Alternate Binding Modes: Structure–Activity Relationship, Structural Characterization, Kinase Profiling, and Cellular Proof of Concept
  作者：Liam Hudson、James Mui、Santiago Vázquez、Diana M. Carvalho、Eleanor Williams、Chris Jones、Alex N. Bullock、Swen Hoelder

  DOI：10.1021/acs.jmedchem.8b00782

  日期：2018.8.23

  Structure-activity relationship and crystallographic data revealed that quinazolinone-containing fragments flip between two distinct modes of binding to activin receptor-like kinase-2 (ALK2). We explored both binding modes to discover potent inhibitors and characterized the chemical modifications that triggered the flip in binding mode. We report kinase selectivity and demonstrate that compounds of

  构效关系和晶体学数据表明，含有喹唑啉酮的片段在两种不同的与激活素受体样激酶-2 (ALK2) 结合的模式之间翻转。我们探索了两种结合模式以发现有效的抑制剂，并表征了触发结合模式翻转的化学修饰。我们报告激酶选择性并证明该系列化合物可调节癌细胞中的 ALK2。这些抑制剂是发现更先进的 ALK2 抑制剂的有吸引力的起点。
• [EN] QUINAZOLINONE DERIVATIVES AND THEIR USE AS B-RAF INHIBITORS<br/>[FR] DÉRIVÉS DE QUINAZOLINONE ET UTILISATION DE CES DÉRIVÉS EN TANT QU'INHIBITEURS DU B-RAF
  申请人：ASTRAZENECA AB

  公开号：WO2006024834A1

  公开（公告）日：2006-03-09

  The invention relates to chemical compounds of the formula (I): or pharmaceutically acceptable salts thereof, which possess B Raf inhibitory activity and are accordingly useful for their anti cancer activity and thus in methods of treatment of the human or animal body. The invention also relates to processes for the manufacture of said chemical compounds, to pharmaceutical compositions containing them and to their use in the manufacture of medicaments of use in the production of an anti-cancer effect in a warm blooded animal such as man.

  该发明涉及化学式(I)的化合物或其药学上可接受的盐，具有B Raf抑制活性，因此在抗癌活性方面有用，并且在治疗人体或动物体的方法中有用。该发明还涉及制备所述化学化合物的方法，含有它们的药物组合物以及它们在制造用于在温血动物（如人类）中产生抗癌效果的药物中的使用。