1-(3'-coumarinyl)-3-(2''-furyl)-2-propen-1-one | 120996-76-1

• 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
• 英文名称: 1-(3'-coumarinyl)-3-(2''-furyl)-2-propen-1-one
• 英文别名: 3-(3-(furan-2-yl) acryloyl)-2H-chromen-2-one；3-(3-(furan-2-yl)acryloyl)-2H-chromen-2-one；3-[3-(Furan-2-yl)prop-2-enoyl]chromen-2-one
• CAS: 120996-76-1
• 化学式: C₁₆H₁₀O₄
• 分子量: 266.253
• InChiKey: XASBDPUGQRZKQT-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  476.0±45.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3'-coumarinyl)-3-(2''-furyl)-2-propen-1-one 在 哌啶 、 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 反应 11.5h， 生成 3-(5-amino-4-(furan-2-yl)-6,7,8,9-tetrahydro-4H-pyrano[2,3-b]quinolin-2-yl)-2H-chromen-2-one
  参考文献：
  名称：

  A comprehensive synthesis and antimicrobial evaluation of some fused heterocycles based on coumarin moiety

  摘要：

  Chalcones and coumarins represent significant naturally occurring plant constituents which exhibit a wide array of pharmacological and biological activities. Herein, synthesis of coumarin-chalcone hybrid derivatives was achieved in a good yield via Claisen-Schmidt aldolic condensation reaction employing 3-acetylcoumarin as a precursor. The reaction of the new chalcones with malononitrile gave rise to a new substituted pyran ring attached to a coumarin moiety. Subsequently, various C-nucleophiles were allowed to react with 3-(4H-pyran-2-yl)coumarin derivative 2a in order to construct novel fused and attached heterocyclic rings bearing different valuable function groups through simple and straightforward reactions. Finally, the antimicrobial activity of the synthesized compounds was evaluated against both Gram-positive and Gram-negative bacteria using Amoxicillin as a standard drug.[GRAPHICS].

  DOI：

  10.24820/ark.5550190.p010.674
• 作为产物：
  描述：

  水杨醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 1-(3'-coumarinyl)-3-(2''-furyl)-2-propen-1-one
  参考文献：
  名称：

  新型香豆素-查尔酮衍生物：乙酰胆碱酯酶、α-糖苷酶和碳酸酐酶抑制剂的合成、表征、抗氧化、循环伏安法、分子建模和生物学评价研究

  摘要：

  在这项研究中，共合成了 12 种香豆素-查尔酮衍生物，其中 6 种是原始的。通过 1H NMR、13C NMR、IR 和元素分析方法 （7g-7l） 阐明新合成化合物的结构。使用 CUPRAC 方法测量的抗氧化效力（Trolox 等效总抗氧化能力）如下： 7j > 7i > 7c > 7d > 7k > 7l > 7f > 7h > 7e > 7g > 7a >7b。此外，还针对人碳酸酐酶 I、II、乙酰胆碱酯酶和 α-糖苷酶评估了这些化合物。与标准乙酰唑胺相比，化合物 7c、7e、7g、7i、7j 和 7l 显示出有希望的人碳酸酐酶 I 抑制作用（Ki：16.64 ± 4.72–49.82 ± 5.82 nM vs Ki：57.64 ± 5.41 nM）。此外，所有化合物对乙酰胆碱酯酶和 α-糖苷酶均表现出很强的抑制作用。乙酰胆碱酯酶的 Ki 值在 2.39 ± 0.97–9.35 ± 3

  DOI：

  10.1016/j.cbi.2023.110655

文献信息

• Microwave-assisted synthesis and evaluation of antimicrobial activity of 3-{3-(s-aryl and s-heteroaromatic)acryloyl}-2<i>H</i>-chromen-2-one derivatives
  作者：Olayinka O. Ajani、Obinna C. Nwinyi

  DOI：10.1002/jhet.298

  日期：——

  analytical and spectral data. All the synthesized compounds were screened for their antibacterial activity and 3-3-(4-dimethylaminophenyl)acryloyl}-2H-chromen-2-one () was discovered to be the most active at minimum inhibitory concentration (MIC) value of 7.8 μg/mL. J. Heterocyclic Chem., (2010).

  在本文中，利用缩合反应的方法对微波作为杂环合成能源的潜在利用进行了探索。3-乙酰香豆素（）与芳族和杂芳族醛形成相应的芳族查耳酮（）和杂芳族查耳酮（ 和 ）分别在1-3分钟内达到良好或优异的产量。化学结构通过分析和光谱数据证实。所有合成的化合物筛选它们的抗菌活性和3- 3-（4-二甲基氨基苯基）丙烯酰基} -2- ħ -色烯-2-酮（发现）在7.8μg/ mL的最小抑菌浓度（MIC）值下活性最高。J.杂环化​​学。（2010）。
• Hybrid Pharmacophoric Approach in the Design and Synthesis of Coumarin Linked Pyrazolinyl as Urease Inhibitors, Kinetic Mechanism and Molecular Docking
  作者：Aamer Saeed、Parvez Ali Mahesar、Pervaiz Ali Channar、Fayaz Ali Larik、Qamar Abbas、Mubashir Hassan、Hussain Raza、Sung-Yum Seo

  DOI：10.1002/cbdv.201700035

  日期：2017.8

  5q showed significant activity against Urease enzyme and also exhibited good antioxidant potential. The compound 3‐(2‐oxo‐2H‐chromen‐3‐yl)‐5‐phenyl‐4,5‐dihydro‐1H‐pyrazole‐1‐carbothioamide (5n) was found to be superior agent in the series with an IC50 = 0.358 ± 0.017 μm compared to standard thiourea with an IC50 = 4720 ± 174 μm. To undermine the binding mode of inhibition kinetic studies were performed

  目前的研究文章报道了香豆素基吡唑啉基硫代酰胺衍生物的合成及其作为杰克豆脲酶抑制剂的生物活性。通过氨基硫脲与新合成的查耳酮反应合成香豆基吡唑啉基硫代酰胺，以良好的收率提供产物，并通过重结晶纯化合成的化合物。香豆素基吡唑啉基硫代酰胺衍生物 5a - 5q 对脲酶显示出显着的活性，并且还表现出良好的抗氧化潜力。发现化合物 3-(2-oxo-2H-chromen-3-yl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (5n) 是该系列中的优良药物，IC50 = 0.358 ± 0.017 μm，与标准硫脲相比，IC50 = 4720 ± 174 μm。为了破坏抑制的结合模式，对大多数有效衍生物进行了动力学研究，发现化合物 5n 通过非竞争性抑制模式抑制脲酶。进行分子对接研究以描绘合成衍生物的结合亲和力。
• Spectroscopic and Biophysical Studies on Chalcones and Schiff Bases Derived from Chromen-2-one and Quinoline-2(1H)-one Derivatives as Antibacterial Agents
  作者：Saad H. Alotaibi

  DOI：10.14233/ajchem.2020.22604

  日期：——

  A series of chalcone derivatives and arylidene analogues derived from 3-acetyl coumarin were synthesized. The synthesized compounds were elucidated by spectroscopic analysis such as elemental analysis, infrared, 1H & 13C NMR and mass spectroscopies, and then the synthesized compounds were purified and tested against three bacterial strains. Compound 9c showed high activity against E. coli and P. aeruginosa. Compounds 4 and 6a showed moderate activity against E. coli while compounds 6a, 6b and 9c showed moderate activity against S. aureus. The reference antibiotics were tested against the same bacteria strains in the same conditions and showed that ciprofloxacin have positive activity against P. aeruginosa and S. aureus but it shows negative activity against E. coli while amoxicillin have positive activity against S. aureus and negative activity against E. coli and P. aeruginosa. On the other hand, vancomycin has positive activity against P. aeruginosa but not tested against E. coli and S. aureus. Staph strains were treated with compounds 4 and 7 on DNA fragmentation and DNA cleavage. Docking studies of synthesized compound 9c was determined and the results were compared with ampicillin. Finally, UV and fluorescence analyses of the synthesized compounds (3, 4, 6b, 6c, 6e, 7, 9c and 9e) were also conducted.

  一系列由3-乙酰基香豆素合成的茶酮衍生物和芳基亚甲基类似物被合成。这些合成化合物通过元素分析、红外、1H和13C NMR以及质谱分析进行了阐明，然后这些合成化合物被纯化并对三种细菌菌株进行了测试。化合物9c对大肠杆菌和铜绿假单胞菌表现出高活性。化合物4和6a对大肠杆菌表现出中等活性，而化合物6a、6b和9c对金黄色葡萄球菌表现出中等活性。参考抗生素在相同条件下对相同的细菌菌株进行了测试，结果显示环丙沙星对铜绿假单胞菌和金黄色葡萄球菌具有正活性，但对大肠杆菌具有负活性，而阿莫西林对金黄色葡萄球菌具有正活性，但对大肠杆菌和铜绿假单胞菌具有负活性。另一方面，万古霉素对铜绿假单胞菌具有正活性，但未对大肠杆菌和金黄色葡萄球菌进行测试。化合物4和7对DNA断裂和DNA切割的金黄色葡萄球菌进行了处理。合成化合物9c的对接研究已确定，并与氨苄青霉素进行了比较。最后，还进行了合成化合物（3、4、6b、6c、6e、7、9c和9e）的UV和荧光分析。
• Bismuth triflate: A highly efficient catalyst for the synthesis of bio-active coumarin compounds via one-pot multi-component reaction
  作者：Mahmoud. Abd El Aleem. Ali. Ali. El-Remaily

  DOI：10.1016/s1872-2067(14)60308-9

  日期：2015.7

  A series of coumarin-chalcone hybrid compounds and coumarins linked to pyrazoline was synthesized in good yield and short time using a simple and efficient method. This method involved the one-pot reaction of salicylaldehyde, an alpha-ketoester and an aromatic aldehyde (in the case of the coumarin-chalcone derivatives) in addition to hydrazine hydrate (in the case of the pyrazolyl coumarins) in the presence of a catalytic amount of bismuth triflate [Bi(OTf)(3), 5 mol%]. The synthesized compounds showed scavenging activity towards the free radical 2,2-diphenyl-1-picrylhydrazyl. All compounds were characterized using IR, H-1 NMR and C-13 NMR spectroscopy. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
• A Convenient Synthesis of Novel Coumarin Derivatives with Anticipated Antimicrobial Activities
  作者：Asmaa Kamal Mourad、Abd El-Naby Ibrahim Essawy、Hussein Abdel-Azim Younus

  DOI：10.3987/com-17-13779

  日期：——

  Chalcone and coumarin are two substantial classes of natural products possessing significant antimicrobial activities. Hybrid compounds containing both structures have been synthesized in a good yield using Claisen-Schmidt aldolic condensation. The reaction of the new chalcones with active methylene compounds under different reaction conditions led to the construction of pyridine, pyran, pyrazole and pyridinone containing coumarin moiety with different functional groups. Investigating the antimicrobial activity of the new synthesized heterocycles, displays that 3-(2'-amino-3'-cyano-4'-(4-hydroxy-3-methoxyphenyly)pyrid-6'-yl)-coumarin 2a has the highest antimicrobial activity toward both Gram-positive and Gram-negative bacteria. Consequently, it was utilized as starting material for synthesis of more new fused heterocycles with anticipated high biological activity. All the new compounds are well characterized using, elemental analysis, FT-IR, H-1 NMR, ESI-Mass Spectrum and tested for their antimicrobial activity.