6-甲氧基-4(1H)-喹唑啉酮 | 19181-64-7

• 物质功能分类: 有机原料 - 酮类化合物
• 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-甲氧基-4(1H)-喹唑啉酮
• 中文别名: 4-羟基-6-甲氧基喹唑啉；6-甲氧基-4-喹唑啉酮
• 英文名称: 6-methoxyquinazolin-4(3H)-one
• 英文别名: 6-methoxy-(3H)-quinazolin-4-one；6-methoxy-4-hydroxyquinazoline；6-Methoxyquinazolin-4-one；6-Methoxyquinazolin-4-OL；6-methoxy-3H-quinazolin-4-one
• CAS: 19181-64-7
• 化学式: C₉H₈N₂O₂
• mdl: MFCD05662727
• 分子量: 176.175
• InChiKey: NOFVNLZQAOGUIT-UHFFFAOYSA-N

物化性质

• 熔点：
  242-243℃
• 沸点：
  361.8±44.0 °C(Predicted)
• 密度：
  1.32

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

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：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Hydroxy-6-methoxyquinazoline
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: 4-Hydroxy-6-methoxyquinazoline
CAS number: 19181-64-7

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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: C9H8N2O2
Molecular weight: 176.2

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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

反应信息

• 作为反应物：
  描述：

  6-甲氧基-4(1H)-喹唑啉酮 在 三氯氧磷 作用下， 反应 12.0h， 以65%的产率得到4-氯-6-甲氧基喹唑啉
  参考文献：
  名称：

  喹唑啉和酞嗪衍生物作为阿戈美拉汀的新型褪黑激素受体配体类似物。

  摘要：

  为了通过调节其药代动力学特性来进一步开发阿戈美拉汀的继任者，我们在此报告了一个新的褪黑激素受体配体家族的设计、合成和药理学结果。由于引入了喹唑啉和酞嗪支架，该支架带有一个乙酰胺侧链和一个甲氧基，作为先前开发的阿戈美拉汀的生物等排配体类似物。将制备的类似物的生物活性与阿戈美拉汀的生物活性进行比较。喹唑啉和酞嗪环被证明是一种多功能支架，可用于简单可行的 MT1 和 MT2 配体。获得了具有亚微摩尔结合亲和力的有效激动剂。然而，与母体化合物相比，两个氮原子的存在导致化合物对 MT1 和 MT2 的亲和力较低，

  DOI：

  10.1016/j.ejmech.2020.112078
• 作为产物：
  描述：

  5-甲氧基-2-硝基苯甲酸 在 盐酸 、 tin(ll) chloride 作用下， 生成 6-甲氧基-4(1H)-喹唑啉酮
  参考文献：
  名称：

  喹唑啉衍生物；合成4-（4'-二乙基氨基-1'-甲基丁基氨基）-6-甲氧基喹唑啉（SN 12,253）。

  摘要：

  DOI：

  10.1021/ja01211a056

文献信息

• Aurora Kinase Modulators and Method of Use
  申请人：Amgen Inc.

  公开号：US20140336182A1

  公开（公告）日：2014-11-13

  The present invention relates to chemical compounds having a general formula I wherein A 1-8 , D′, L 1 , L 2 , R 1 , R 6-8 and n are defined herein, and synthetic intermediates, which are capable of modulating various protein kinase receptor enzymes and, thereby, influencing various disease states and conditions related to the activities of such kinases. For example, the compounds are capable of modulating Aurora kinase thereby influencing the process of cell cycle and cell proliferation to treat cancer and cancer-related diseases. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of Aurora kinase.

  本发明涉及具有一般式I的化合物，其中A1-8、D'、L1、L2、R1、R6-8和n在此处定义，并且具有调节各种蛋白激酶受体酶并因此影响与这些激酶活动相关的各种疾病状态和病况的能力的合成中间体。例如，这些化合物能够调节枢纽激酶，从而影响细胞周期和细胞增殖过程，以治疗癌症和与癌症相关的疾病。该发明还包括包括这些化合物的药物组合物，以及治疗与枢纽激酶活性相关的疾病状态的方法。
• 4-Aminoquinazoline Derivatives and Uses Thereof
  申请人：SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY

  公开号：US20140235633A1

  公开（公告）日：2014-08-21

  The present invention provides a 4-aminoquinazoline derivative having the chemical structure of the following formula, and the use thereof. It is demonstrated by the pharmacological experiment that, the compound or a salt thereof according to the present invention not only has distinct inhibitory effect on histone deacetylases, but also has stronger differentiation induction and anti-proliferative activities for certain tumor cells. It can be used in the treatment of cancers and diseases related to cell differentiation and proliferation. Excellent efficacy is observed especially for leukemia and a solid tumor. As demonstrated by the animal test, the compound or a salt thereof according to the present invention is less toxic.

  本发明提供了一种具有以下化学结构的4-氨基喹唑啉衍生物，以及其用途。药理实验证明，根据本发明的化合物或其盐不仅对组蛋白去乙酰化酶具有明显的抑制作用，而且对某些肿瘤细胞具有更强的分化诱导和抗增殖活性。它可用于治疗与细胞分化和增殖相关的癌症和疾病。特别是对白血病和实体肿瘤观察到了出色的疗效。药物实验证明，根据本发明的化合物或其盐毒性较小。
• Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives
  作者：Bin Sun、Rongcheng Shi、Kesheng Zhang、Xiaoli Tang、Xiayue Shi、Jiayun Xu、Jin Yang、Can Jin

  DOI：10.1039/d1cc02415a

  日期：——

  A novel and green strategy for the synthesis of acylated quinazolinone derivatives via photo-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without

  已经开发了通过光诱导的带有未活化烯烃的喹唑啉酮的脱羧级联自由基酰化/环化反应来合成酰化喹唑啉酮衍生物的新颖和绿色策略。该协议提供了一种通过自催化能量转移过程从α-酮酸中获取酰基的新颖途径。最重要的是，该反应在没有任何外部光催化剂，添加剂或氧化剂的情况下可顺利进行，并且在阳光照射下，在流动条件下很容易按比例放大。
• Efficient and selective microwave-assisted copper-catalyzed synthesis of quinazolinone derivatives in aqueous
  作者：Fang Ke、Caiqin Liu、Peng Zhang、Jianhua Xu、Xiaole Chen

  DOI：10.1080/00397911.2018.1533974

  日期：2018.12.17

  Abstract Microwave-assisted copper-catalyzed cascade reactions between 2-halobenzoic acids and amidines to synthesize quinazolinone derivatives in water are reported. A variety of target products were obtained in good to excellent yields up to 94%. Its application was performed by the synthesis of 4-(1H-benzo[d]imidazol-2-ylthio)-6-methoxypteridine, which displayed significant anti-proliferation effect

  摘要 微波辅助铜催化 2-卤代苯甲酸和脒之间的级联反应在水中合成喹唑啉酮衍生物。获得了多种目标产品，产率高达 94%。其应用是通过合成4-(1H-苯并[d]咪唑-2-基硫基)-6-甲氧基蝶啶而进行的，具有显着的抗增殖作用。图形摘要
• Trans-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acid derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04281127A1

  公开（公告）日：1981-07-28

  Trans-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acid derivatives of the formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, lower cycloalkyl, lower alkoxy, hydroxy, halo, lower alkykthio, lower alkylsulfinyl, lower alkylsulfonyl, di-(C.sub.1 -C.sub.7)alkyl-N(CH.sub.2).sub.n O-- or 2-hydroxyethoxy; R.sub.2 is hydrogen, lower alkyl or lower alkoxy; R.sub.3 is hydroxy, lower alkoxy, di-(C.sub.1 -C.sub.7)alkyl-N(CH.sub.2).sub.n O-- or di-(C.sub.1 -C.sub.7)alkyl-N(CH.sub.2).sub.n NH--; and n is 2 to 7; provided that at least one of R.sub.1 and R.sub.2 is other than hydrogen, when R.sub.3 is hydroxy, a salt thereof with a pharmaceutically acceptable base, or when R.sub.3 is di-(C.sub.1 -C.sub.7)alkyl-N(CH.sub.2).sub.n O-- or di-(C.sub.1 -C.sub.7)alkyl-N(CH.sub.2).sub.n NH--, a salt thereof with a pharmaceutically acceptable acid, and a process for the preparation thereof, are described. The compounds of formula I are useful as agents in the prevention of allergic reactions.

  公式为##STR1##的Trans-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acid衍生物，其中R.sub.1为氢、较低烷基、较低环烷基、较低烷氧基、羟基、卤素、较低烷硫基、较低烷基磺基、较低烷基砜基、二-(C.sub.1 -C.sub.7)烷基-N(CH.sub.2).sub.n O--或2-羟基乙氧基；R.sub.2为氢、较低烷基或较低烷氧基；R.sub.3为羟基、较低烷氧基、二-(C.sub.1 -C.sub.7)烷基-N(CH.sub.2).sub.n O--或二-(C.sub.1 -C.sub.7)烷基-N(CH.sub.2).sub.n NH--；n为2至7；要求至少R.sub.1和R.sub.2中的一个不是氢，当R.sub.3为羟基时，其与药用可接受的碱的盐，或当R.sub.3为二-(C.sub.1 -C.sub.7)烷基-N(CH.sub.2).sub.n O--或二-(C.sub.1 -C.sub.7)烷基-N(CH.sub.2).sub.n NH--时，其与药用可接受的酸的盐，以及其制备方法。公式I的化合物可用作预防过敏反应的药物。