3-乙酰基-7-甲氧基香豆素 | 64267-19-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 3-乙酰基-7-甲氧基香豆素
• 英文名称: 3-acetyl-7-methoxycoumarin
• 英文别名: 3-acetyl-7-methoxy-2H-chromen-2-one；3-acetyl-7-methoxy-2H-1-benzopyran-2-one；3-acetyl-7-methoxychromen-2-one
• CAS: 64267-19-2
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: HJRFKKRMCGZIOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Acetyl-7-methoxychromen-2-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: 3-Acetyl-7-methoxychromen-2-one
CAS number: 64267-19-2

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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: C12H10O4
Molecular weight: 218.2

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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.

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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：

  3-乙酰基-7-甲氧基香豆素 在 四丁基溴化铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1-cyclopropyl-6-fluoro-8-methoxy-7-{4-[2-(7-methoxycoumarin-3-yl)-2-oxo]ethyl-3-methylpiperazin-1-yl}-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  含有香豆素部分的氟喹诺酮衍生物的合成和体外抗分枝杆菌活性

  摘要：

  设计、合成了一系列加替沙星、环丙沙星和 8-OCH3 环丙沙星香豆素衍生物，与母体氟喹诺酮类药物相比，亲油性显着提高，并通过 1H-NMR、MS 和 HRMS 进行表征。评估了这些衍生物对耻垢分枝杆菌 CMCC 93202 和 MTB H37Rv ATCC 27294 的体外活性。所有合成的化合物对耻垢分枝杆菌 CMCC 93202 的活性均低于母体化合物，但发现化合物 6 的活性为比环丙沙星、8-OCH3 环丙沙星、莫西沙星和利福平强 2-8 倍，与加替沙星对抗 MTB H37Rv ATCC 27294 的效果相当。这些结果表明测试化合物的亲脂性不是影响抗分枝杆菌活性的唯一参数。

  DOI：

  10.1002/ardp.201000256
• 作为产物：
  描述：

  2,4-二羟基苯甲醛 在 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 3-乙酰基-7-甲氧基香豆素
  参考文献：
  名称：

  香豆素-查尔酮杂种作为MAO-B的抑制剂：生物活性和计算机模拟研究

  摘要：

  合成了十四种在香豆素的C3碳原子上被α，β-不饱和酮改性的香豆素衍生的化合物。这些化合物可以被称为查库香豆素（3-肉桂酰基-2 H-色氨酸-2-酮）。查耳酮和香豆素在药物化学中都是公认的支架，具有多种生物学和药理学特性，其中神经保护活性和多种酶抑制作用（包括线粒体酶系统）脱颖而出。对单胺氧化酶B（MAO-B）抑制剂的评估引起了人们对于帕金森氏症等神经退行性疾病治疗剂的浓厚兴趣。在此处评估的针对MAO-B的14种硫氰酸酯中，ChC4表现出最强的体外活性，IC 50= 0.76±0.08 µM。计算对接，分子动力学和MM / GBSA研究，证实ChC4非常稳定地结合到活性rMAO-B位点，解释了实验抑制数据。

  DOI：

  10.3390/molecules26092430

文献信息

• 香豆素曼尼希碱及其在防治神经退行性疾病中的用途
  申请人：中国医学科学院药物研究所

  公开号：CN108203423A

  公开（公告）日：2018-06-26

  本发明涉及一类新的香豆素曼尼希碱及其药学上可接受的盐，这类化合物的制备方法，含有这类化合物的药物组合物，这类化合物在制备预防或治疗神经退行性疾病药物中的应用，尤其是在制备预防或治疗阿尔茨海默病、帕金森氏病、肌肉萎缩性侧索硬化症、多发性硬化病药物中的应用。
• The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study
  作者：Olimpo García-Beltrán、Natalia Mena、Edwin G. Pérez、Bruce K. Cassels、Marco T. Nuñez、Francisca Werlinger、Daniel Zavala、Margarita E. Aliaga、Paulina Pavez

  DOI：10.1016/j.tetlet.2011.09.137

  日期：2011.12

  (Cys), glutathione (GSH) and other biothiols, such as homocysteine (Hcy) and cysteinyl-glycine (Cys-Gly), were developed. These molecular probes are coumarin-based derivatives containing a chalcone-like moiety that reacts with biothiols through a Michael addition reaction, leading to strong fluorescence enhancements. The reactivity of the tested biothiols toward both probes (ChC1 and ChC2) follows

  开发了两种用于检测半胱氨酸（Cys），谷胱甘肽（GSH）和其他生物硫醇（如高半胱氨酸（Hcy）和半胱氨酰甘氨酸（Cys-Gly））的荧光探针。这些分子探针是基于香豆素的衍生物，包含查尔酮样部分，该部分通过迈克尔加成反应与生物硫醇反应，从而导致强烈的荧光增强。被测试的生物硫醇对两种探针（ChC1和ChC2）的反应性依次为Cys> GSH> Hcy> Cys-Gly，ChC1的反应性不如ChC2。评估了对其他氨基酸的可能干扰。ChC1和ChC2 展示了使用硫醇的高度选择性荧光增强作用，使这些探针可用于SH-SY5Y细胞中的荧光硫醇测定。
• Green and Rapid Access to Benzocoumarins<i>via</i>Direct Benzene Construction through Base-Mediated Formal [4+2] Reaction and Air Oxidation
  作者：Chengli Mou、Tingshun Zhu、Pengcheng Zheng、Song Yang、Bao-An Song、Yonggui Robin Chi

  DOI：10.1002/adsc.201500771

  日期：2016.3.3

  typically with an intramolecular ester forming reaction to make the lactone ring as the last step. Another major method involves transition metal‐catalyzed coupling or carbon‐hydrogen bond activation reactions starting with pre‐existing aryl frameworks in the substrates. Here we report a new strategy for the green and rapid access to benzocoumarins and their derivatives. Our method uses readily available

  苯并香豆素是在天然产物和合成分子中广泛发现的重要结构基序。合成苯并香豆素及其衍生物的传统方法需要多个步骤，通常需要进行分子内酯形成反应以使内酯环成为最后一步。另一种主要方法涉及过渡金属催化的偶联或碳氢键活化反应，该反应从底物中预先存在的芳基骨架开始。在这里，我们报告了绿色和快速获得苯并香豆素及其衍生物的新策略。我们的方法使用容易获得的不饱和醛和香豆素作为底物，使用空气作为绿色氧化剂。整个反应通过正式的[4 + 2]过程进行，以构建新的苯环，从而基本上在单个步骤中得到苯并香豆素。没有使用金属催化剂。不涉及有毒或昂贵的试剂。我们的新方法的强大功能在大麻素（一种具有生物活性的天然产物）的简明正式全合成中得到了进一步证明。
• Discovery of coumarin Mannich base derivatives as multifunctional agents against monoamine oxidase B and neuroinflammation for the treatment of Parkinson's disease
  作者：Deng Tao、Yue Wang、Xiu-Qi Bao、Bei-Bei Yang、Fan Gao、Lin Wang、Dan Zhang、Li Li

  DOI：10.1016/j.ejmech.2019.04.016

  日期：2019.7

  achieve better results. In this study, a series of coumarin Mannich base derivatives were designed and synthesized as multifunctional agents for PD treatment. Among the derivatives, 3-(3-(dimethylamino)propanoyl)-7-hydroxy-5-methyl- 2H-chromen-2-one hydrochloride (24) exhibited the most potent and selective hMAO-B inhibitory activity, and anti-inflammatory and neuroprotective effects in the in vitro studies

  由于帕金森氏病（PD）发病机理的复杂性，多模式治疗可能会取得更好的结果。在这项研究中，设计并合成了一系列香豆素曼尼希碱衍生物作为用于PD治疗的多功能药物。在衍生物中，3-（3-（二甲基氨基）丙酰基）-7-羟基-5-甲基-2H-铬-2-酮盐酸盐（24）表现出最强效和选择性的h MAO-B抑制活性，并具有抗在体外研究中具有炎症和神经保护作用。在1-甲基-4-苯基-1,2,3,6-四氢吡啶（MPTP）诱导的PD小鼠模型中，它显着减轻了PD相关的行为缺陷。此外，初步的力学研究表明，24可以选择性抑制MAO-B活性，减少神经炎症过程，并保护酪氨酸羟化酶免疫阳性的多巴胺能神经元。这些结果表明24是有效治疗PD的有前途的多功能药物。
• An investigation on 3-acetyl-7-methoxy-coumarin Schiff bases and their Ru(<scp>ii</scp>) metallates with potent antiproliferative activity and enhanced LDH and NO release
  作者：G. Kalaiarasi、S. Rex Jeya Rajkumar、S. Dharani、J. G. Małecki、R. Prabhakaran

  DOI：10.1039/c7ra12104k

  日期：——

  New cyclometallated ruthenium(ii) complexes of 3-acetyl-7-methoxycoumarin-4N-substituted thiosemicarbazones were synthesized and characterized by analytical and spectral techniques.

  新的3-乙酰基-7-甲氧基香豆素-4N-取代硫脲酮基环金属钌（II）配合物已经合成，并通过分析和光谱技术进行了表征。