7-甲氧基-2-氧代-2H-色烯-3-羧酸乙酯 | 6093-72-7

• 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: 7-甲氧基-2-氧代-2H-色烯-3-羧酸乙酯
• 英文名称: 7-methoxycoumarin-3-carboxylic acid ethyl ester
• 英文别名: ethyl 7-methoxy-2-oxo-2H-chromene-3-carboxylate；ethyl 7-methoxycoumarin-3-carboxylate；ethyl 7-methoxy-2-oxochromene-3-carboxylate
• CAS: 6093-72-7
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: FWFVXBZXJKTVGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

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: Ethyl 7-methoxy-2-oxochromene-3-carboxylate
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: Ethyl 7-methoxy-2-oxochromene-3-carboxylate
CAS number: 6093-72-7

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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.
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
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C13H12O5
Molecular weight: 248.2

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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：

  7-甲氧基-2-氧代-2H-色烯-3-羧酸乙酯 在 氯化亚砜 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-氯甲酰基-7-甲氧基香豆素
  参考文献：
  名称：

  香豆素衍生物作为新型乙酰胆碱酯酶抑制剂的设计，合成和生物学评估，该抑制剂可减轻H 2 O 2诱导的SH-SY5Y细胞凋亡

  摘要：

  设计，合成和研究了一系列新的香豆素衍生物以抑制胆碱酯酶，包括乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）。这项生物学研究表明，这些含有哌嗪环的化合物对AChE而不是BuChE具有明显的抑制活性。进一步的研究表明，9x作为这种结构衍生物之一，对AChE表现出最强的抑制活性，IC 50值为34 nM。此外，分子对接，流式细胞术（FCM）和蛋白质印迹试验表明9x可以诱导细胞保护性自噬以减弱H 2 O 2。诱导的神经母细胞瘤SH-SY5Y细胞死亡。这些发现凸显了一种新的方法，可用于开发针对AChE的新型潜在神经保护化合物，该化合物在未来的阿尔茨海默氏病（AD）治疗中具有自噬诱导活性。

  DOI：

  10.1016/j.bioorg.2016.07.013
• 作为产物：
  描述：

  3-氯甲酰基-7-甲氧基香豆素 在 乙醇 作用下， 生成 7-甲氧基-2-氧代-2H-色烯-3-羧酸乙酯
  参考文献：
  名称：

  Baker; Collis, Journal of the Chemical Society, 1949, p. Spl. 12, 14

  摘要：

  DOI：

文献信息

• Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives
  作者：Daniela Secci、Simone Carradori、Adriana Bolasco、Paola Chimenti、Matilde Yáñez、Francesco Ortuso、Stefano Alcaro

  DOI：10.1016/j.ejmech.2011.07.017

  日期：2011.10

  Several 3-carbonyl (1–26), 3-acyl (27–52), and 3-carboxyhydrazido (53–58) coumarins have been synthesized in high yields (72–99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl

  几个-3-羰基（1 - 26），3-酰基（27 - 52），和3- carboxyhydrazido（53 - 58）香豆素已经以高收率（72-99％）合成并测试在体外对它们的人类单胺氧化酶A和B（hMAO-A和hMAO-B）的抑制活性。评价了香豆素核上的不同取代基对生物活性和同工型选择性的影响。对于使用IC 50获得高效且选择性的hMAO-B抑制剂而言，在3-乙酯香豆素环的C7位取代或在C3引入肼基取代基很重要。值在纳摩尔范围内。一些衍生物也进行了稳定性测试，在体外没有化​​学裂解。
• Synthesis of coumarin-3-carboxylic esters via FeCl3-catalyzed multicomponent reaction of salicylaldehydes, Meldrum's acid and alcohols
  作者：Xinwei He、Yongjia Shang、Yao Zhou、Zhiyu Yu、Guang Han、Wenjing Jin、Jiaojiao Chen

  DOI：10.1016/j.tet.2014.12.042

  日期：2015.2

  FeCl3-catalyzed multicomponent reaction was developed for the facile synthesis of coumarin-3-carboxylic ester derivatives in a highly atom-economic and environmentally friendly way. Using simple and cheaply available salicylaldehydes, Meldrum's acid and alcohols as the starting materials, the method needs no extra additives and features wide substrate scope, good functional group tolerance and mild reaction conditions

  开发了FeCl 3催化的多组分反应，以高度原子经济和环境友好的方式容易地合成香豆素-3-羧酸酯衍生物。该方法使用简单廉价的水杨醛，Meldrum的酸和醇作为起始原料，不需要额外的添加剂，并且具有广泛的底物范围，良好的官能团耐受性和温和的反应条件。
• Synthesis of coumarin analogs appended with quinoline and thiazole moiety and their apoptogenic role against murine ascitic carcinoma
  作者：T. Prashanth、B.R. Vijay Avin、Prabhu Thirusangu、V. Lakshmi Ranganatha、B.T. Prabhakar、J.N. Narendra Sharath Chandra、Shaukath Ara Khanum

  DOI：10.1016/j.biopha.2019.108707

  日期：2019.4

  The synthesis and antiproliferative effect of a series of quinoline and thiazole containing coumarin analogs 12a-d and 13a-f respectively, on mice leukemic cells was performed. The chemical structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectral analysis. The result indicates that, 7-methoxy-2-oxo-2H-chromene-3-carboxylic acid [4-(4-methoxy-phenyl)-thiazol-2-yl]-amide

  进行了一系列分别含有喹啉和噻唑的香豆素类似物12a-d和13a-f的合成和抗增殖作用对小鼠白血病细胞的作用。通过IR，1 H NMR，13 C NMR和质谱分析确认了新合成的化合物的化学结构。结果表明，7-甲氧基-2-氧代-2H-亚甲基-3-羧酸[4-（4-甲氧基-苯基）-噻唑-2-基]-酰胺（13f）对EAC和DLA表现出有效的活性。 MTT（15.3μM），色氨酸蓝（15.6μM）和LDH（14.2μM）泄漏检测中的细胞以5-氟尿嘧啶为标准。此外，通过BrdU掺入，TUNEL，FACS和DNA片段化分析证实了化合物13f对艾氏腹水肿瘤的抗肿瘤作用。实验数据表明，化合物13f通过激活凋亡因子（例如caspase-8＆-3，CAD，Cleaved PARP，γ-H2AX）并降解癌细胞的基因组DNA从而诱导小鼠腹水肿瘤的发展，从而诱导其凋亡。此外，还对化合物13f进行了对接研究，以批准体外和
• Antifungal activity, mode of action variability, and subcellular distribution of coumarin-based antifungal azoles
  作者：Rebecca Elias、Raphael I. Benhamou、Qais Z. Jaber、Orly Dorot、Sivan Louzoun Zada、Keren Oved、Edward Pichinuk、Micha Fridman

  DOI：10.1016/j.ejmech.2019.07.003

  日期：2019.10

  Azole antifungals inhibit the biosynthesis of ergosterol, the fungal equivalent of cholesterol in mammalian cells. Here we report an investigation of the activity of coumarin-substituted azole antifungals. Screening against a panel of Candida pathogens, including a mutant lacking CYP51, the target of antifungal azoles, revealed that this enzyme is inhibited by triazole-based antifungals, whereas imidazole-based

  唑类抗真菌剂抑制麦角固醇的生物合成，麦角固醇是哺乳动物细胞中胆固醇的真菌等同物。在这里，我们报告了香豆素取代的吡咯类抗真菌药活性的调查。针对假丝酵母菌的筛选病原体，包括缺少CYP51的突变体（抗真菌唑的靶标）显示，该酶被三唑类抗真菌剂抑制，而咪唑类衍生物具有多种作用方式。与基于三唑的衍生物相比，带有咪唑的抗真菌剂能更有效地减少与真菌感染的持续和/或复发相关的拖尾生长。咪唑衍生物对哺乳动物细胞的毒性更大，并且更有效地抑制了CYP3A4的活性，而CYP3A4的活性是造成唑类毒性的主要原因之一。使用活细胞成像，我们发现，不管是位于内质网（是CYP51的细胞器）上的吡咯环荧光7-二乙基氨基香豆素基吡咯类化合物。
• ROS Inhibitory Activity and Cytotoxicity Evaluation of Benzoyl, Acetyl, Alkyl Ester, and Sulfonate Ester Substituted Coumarin Derivatives
  作者：Uzma Salar、Khalid M. Khan、Almas Jabeen、Aisha Faheem、Farwa Naqvi、Shakil Ahmed、Erum Iqbal、Farman Ali、Kanwal、Shahnaz Perveen

  DOI：10.2174/1573406415666190826153001

  日期：2020.11.23

  Limited SAR study revealed that the hydroxy-substituted compound showed better ROS inhibition potential in case of 3-benzoyl and 3-ethylester coumarin derivatives. Whereas, chloro substitution was found to be important in case of 3-acetyl coumarin derivatives. Similarly, in case of sulfonate ester, chloro, and nitro groups especially at positions -4 and -3 of ring "R" played vital role in ROS inhibition

  背景许多非甾体抗炎药(NSAID)，包括阿司匹林、消炎痛、布洛芬、氟芬那酸和保泰松在临床上用于治疗炎性疾病。这些非甾体抗炎药与严重的副作用有关，例如胃溃疡、肾毒性和出血。因此，确定有效和安全的炎症性疾病治疗方法仍然是药物化学家非常感兴趣的。方法 使用鲁米诺增强化学发光技术筛选了一系列不同取代的苯甲酰基、乙酰基、烷基酯和磺酸酯取代的香豆素 1-64 对活性氧的抑制作用，活性氧是由酵母聚糖激活的全血吞噬细胞产生的。结果 在所有测试化合物中，8 (IC50 = 65.0 ± 3.1 μM)、24 (IC50 = 41.8 ± 1.5 μM)、26 (IC50 = 10.6 ± 2.8 μM)、28 (IC50 = 20。9 ± 1.5 μM)和 41 (IC50 = 4.6 ± 0.3 μM) 与标准抗炎药布洛芬 (IC50 = 54.3 ± 1.9 μM) 相比显示出良好的抗炎潜力。具体而言，化合物