7-溴喹唑啉-4(3H)-酮 | 194851-16-6

• 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: 7-溴喹唑啉-4(3H)-酮
• 中文别名: 7-溴-4-羟基喹唑啉；7-溴-4(3H)-喹唑啉酮；7-溴-3,4-二氢喹唑啉-4-酮；7-溴-4-喹唑啉酮；7-修喹唑啉-4-酮；7-溴喹唑啉-4-酮
• 英文名称: 7-bromoquinazolin-4(3H)-one
• 英文别名: 7-bromo-3H-quinazolin-4-one；7-Bromoquinazolin-4(3H)-one
• CAS: 194851-16-6
• 化学式: C₈H₅BrN₂O
• mdl: MFCD07838323
• 分子量: 225.044
• InChiKey: FUGKKMYSCAYXJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  350.1±44.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 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：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  应存于室温、密封且干燥的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 7-Bromo-1h-quinazolin-4-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: 7-Bromo-1h-quinazolin-4-one
CAS number: 194851-16-6

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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.
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: C8H5BrN2O
Molecular weight: 225.0

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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

应用

7-溴-3,4-二氢喹唑啉-4-酮是一种喹唑酮化合物。喹唑酮是一类具有良好生物医药活性的含氮杂环化合物，由于其广泛的生物和药物活性。

制备

步骤1: 2-氨基-4-溴苯甲酸甲酯的合成

在室温下，向单口瓶中加入2-氨基-4-溴苯甲酸（12.0g，55.5mmol）和甲醇（200mL），然后在0℃下滴加浓硫酸（12mL）。反应80℃进行48h后终止。将反应冷却至室温并浓缩，随后将残余液体缓慢倒入冰水中，并用饱和NaHCO3溶液调节pH值至8。接着用乙酸乙酯（EA）萃取，有机相用水洗，饱和NaCl水洗，再通过无水硫酸钠（Na2SO4）干燥后过滤并浓缩。最后进行柱层析分离（PE/EA体系），得到白色固体11g，收率87％。

步骤2: 7-溴-3,4-二氢喹唑啉-4-酮的合成

在室温下，向30mL微波管中加入2-氨基-4-溴苯甲酸甲酯（2.5g，10.86mmol）和甲酰胺（18mL）。反应于200℃进行1h后终止。冷却至室温，用乙酸乙酯溶解，并用水洗两次。再通过无水硫酸钠干燥并过滤浓缩。粗品直接用于下一步合成。

反应信息

• 作为反应物：
  描述：

  7-溴喹唑啉-4(3H)-酮 在 三氯氧磷 作用下， 生成 7-溴-4-氯喹唑啉
  参考文献：
  名称：

  脚手架跳策略对细胞周期蛋白G相关激酶抑制剂的鉴定。

  摘要：

  我们最近报道了细胞周期蛋白G相关激酶（GAK）的基于异噻唑并[4,3-b]吡啶的抑制剂的发现，该抑制剂对GAK具有低纳摩尔结合亲和力，并表现出广谱抗病毒活性。为了提出起GAK抑制剂作用的新型核心结构，从两个不同的异噻唑并[4,3-b]吡啶类化合物开始采用了支架跳跃法。总共合成了13种新颖的5,6-和6,6-稠合的双环杂芳族骨架。其中四个显示出GAK亲和力的Kd值处于低微摩尔范围内，可以作为基于不同支架的GAK抑制剂发现的化学起点。

  DOI：

  10.1002/cmdc.201800690
• 作为产物：
  描述：

  2-氨基-4-溴苯甲酸甲酯 在 indium(III) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 7-溴喹唑啉-4(3H)-酮
  参考文献：
  名称：

  角噻唑并[5,4- f ]和[4,5- h ]喹唑啉的新型合成，其线性噻唑并[4,5- g ]和[5,4- g ]喹唑啉类似物的制备

  摘要：

  9-氧代8,9-二氢噻唑[5,4- f ]喹唑啉-2-腈（1）或6-氧代6,7-二氢噻唑[4,5 - h ]喹唑啉-2-腈（2）的合成）进行了重新研究，目的是改变与喹唑啉4-one部分相连的噻唑环的位置，以便合成两个新颖的线性三环式8-氧代-7,8-二氢噻唑并[4,5- g ]喹唑啉- 2-甲腈（3）和8-氧代7,8-二氢噻唑并[5,4 - g ]喹唑啉-2-甲腈（4）。本文描述的途径为获得有效的生物活性杂环化合物文库提供了各种替代和转化途径。

  DOI：

  10.1016/j.tet.2013.02.066

文献信息

• Morpholinylquinazolines
  申请人：Mederski Werner

  公开号：US20130012489A1

  公开（公告）日：2013-01-10

  The invention relates to compounds of the formulae (I), (II) and (III) in which R1, R2, R3, R4, Y, W 1 , W 2 , L, A, Alk, Cyc, Ar, Het 1 , Het 2 , Hal and n have the meaning indicated in claim 1 , and/or physiologically acceptable salts, tautomers and stereo-isomers thereof, including mixtures thereof in all ratios. The compounds of the formula (I) can be used for the inhibition of serine/threonine protein kinases and for the sensitisation of cancer cells to anticancer agents and/or ionising radiation. The invention also relates to the use of the compounds of the formula (I) in the prophylaxis, therapy or progress control of cancer, tumours, metastases or angiogenesis disorders, in combination with radiotherapy and/or an anticancer agent. The invention furthermore relates to a process for the preparation of the compounds of the formula (I) by reaction of compounds of the formulae (II) and (III) and optionally conversion of a base or acid of the compounds of the formula (I) into one of their salts.

  该发明涉及以下式(I)、(II)和(III)的化合物： 其中R1、R2、R3、R4、Y、W1、W2、L、A、Alk、Cyc、Ar、Het1、Het2、Hal和n具有权利要求书中所示的含义，以及/或其生理上可接受的盐、互变异构体和立体异构体，包括所有比例的混合物。式(I)的化合物可用于抑制丝氨酸/苏氨酸蛋白激酶，并使癌细胞对抗癌药物和/或电离辐射敏感。该发明还涉及在放射治疗和/或抗癌药物的联合下使用式(I)的化合物在癌症、肿瘤、转移瘤或血管生成紊乱的预防、治疗或进展控制中。此外，该发明还涉及通过将式(II)和(III)的化合物反应，并可选地将式(I)的化合物的碱或酸转化为它们的盐之一来制备式(I)的化合物的方法。
• [EN] NOVEL HETEROCYCLIC COMPOUNDS AS ANTIMALARIAL AGENTS<br/>[FR] NOUVEAUX COMPOSÉS HÉTÉROCYCLIQUES UTILES EN TANT QU'AGENTS ANTIPALUDIQUES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2015028989A1

  公开（公告）日：2015-03-05

  The invention relates to novel heterocyclic compounds of the Formula I. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more compounds of the Formula I and especially their use as medicaments to treat or prevent malaria infections or to treat or prevent other protozoal diseases like sleeping sickness, Chagas disease, amebiasis, giardiasis, trichomoniasis, toxoplasmosis, and leishmaniasis.

  本发明涉及式I的新颖杂环化合物。本发明还涉及包括制备化合物的方法、包含式I的一个或多个化合物的药物组合物，尤其是它们作为药物用于治疗或预防疟疾感染或治疗或预防其他原虫疾病，如昏睡病、查加斯病、阿米巴病、贾第虫病、滴虫病、弓形虫病和利什曼病。
• [EN] MTH1 INHIBITORS FOR TREATMENT OF CANCER<br/>[FR] INHIBITEURS MTH1 POUR LE TRAITEMENT DU CANCER
  申请人：THOMAS HELLEDAYS STIFTELSE FÖR MEDICINSK FORSKNING

  公开号：WO2015187088A1

  公开（公告）日：2015-12-10

  A compound of formula I, (I) or a pharmaceutically-acceptable salt thereof. The compound is useful in the treatment of cancer.

  公式I的化合物(I)或其药用可接受的盐。该化合物在治疗癌症中很有用。
• [EN] SUBSTITUTED BENZAZINONES AS ANTIBACTERIAL COMPOUNDS<br/>[FR] BENZAZINONES SUBSTITUÉS À UTILISER EN TANT QUE COMPOSÉS ANTIBACTÉRIENS
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2017098440A1

  公开（公告）日：2017-06-15

  The present invention relates to LpxC antibacterial compounds of Formula (1A), corresponding pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions:, compound preparation, treatment methods and uses for bacterial infections, especially those caused by gram-negative bacteria.

  该发明涉及Formula (1A)的LpxC抗菌化合物，其相应的药学上可接受的盐，相应的药物组合物，化合物制备，细菌感染的治疗方法和用途，特别是由革兰氏阴性细菌引起的感染。
• ALKYNE SUBSTITUTED QUINAZOLINE COMPOUND AND METHODS OF USE
  申请人：Newgen Therapeutics, Inc.

  公开号：US20160031860A1

  公开（公告）日：2016-02-04

  The invention provides alkyne substituted quinazoline compounds, such as compounds of the formula (I), which are irreversible ErbB kinase inhibitors. The compounds are useful in the treatment of diseases and disorders where ErbB kinase activity is implicated such as a hyperproliferative disorder (e.g., cancer).

  这项发明提供了炔基取代的喹唑啉化合物，例如式(I)的化合物，这些化合物是不可逆的ErbB激酶抑制剂。这些化合物在治疗ErbB激酶活性参与的疾病和紊乱方面非常有用，比如高增殖性疾病（例如癌症）。