3-(3-bromophenyl)-1-(coumarin-3-yl)prop-2-en-1-one | 193619-96-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(3-bromophenyl)-1-(coumarin-3-yl)prop-2-en-1-one
• 英文别名: 2H-1-Benzopyran-2-one, 3-[3-(3-bromophenyl)-1-oxo-2-propenyl]-；3-[3-(3-bromophenyl)prop-2-enoyl]chromen-2-one
• CAS: 193619-96-4
• 化学式: C₁₈H₁₁BrO₃
• mdl: MFCD05027541
• 分子量: 355.188
• InChiKey: KNMHRSXDMNYIGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-bromophenyl)-1-(coumarin-3-yl)prop-2-en-1-one 、 (4-甲基-2-氧代-2H-色烯-7-氧基)-乙酸肼 在 吡啶 作用下， 反应 6.0h， 以70%的产率得到5-(3-bromophenyl)-3-(2-oxo-2H-chromen-3-yl)-1-(4-methyl-2-oxo-2H-chromen-7-yloxyacetyl)-2-pyrazoline
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Novel Series of 1,3-Dicoumarinyl-5-aryl-2-pyrazolines

  摘要：

  In the present paper novel 1,3,5-trisubstituted 2-pyrazolines (4a-q) were synthesized via condensation of different substituted 3-cinnamoyl-2-oxo-2H-chromenes (2a-q) with 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetohydrazide (3). Chalcones were prepared via Claisen-Schmidt condensation by refluxing 3-acetyl-2-oxo-2H-chromen (1) with corresponding aldehydes in ethanol, in the presence of piperidine. All of these compounds were characterized by means of their IR, (1)H NMR and LC/MS/MS spectroscopic data and elemental microanalysis. Chalcones and pyrazolines were screened for their antioxidant and iron chelating activity.

  DOI：

  10.3987/com-11-12196
• 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 3-(3-bromophenyl)-1-(coumarin-3-yl)prop-2-en-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 of new fluorinated coumarin–pyrimidine hybrids as potent anticancer agents, their DNA cleavage and X-ray crystal studies
  作者：Kallappa. M. Hosamani、Dinesh S. Reddy、Hirihalli. C. Devarajegowda

  DOI：10.1039/c4ra12222d

  日期：——

  Rapid and high yielding synthesis of new fluorinated coumarin–pyrimidine hybrids and their application as potent anticancer agents is described.

  快速高产量合成新的氟化香豆素-嘧啶杂化物，并将其应用作强效抗癌剂。
• Analgesic study of novel pyrimidine derivatives linked with coumarin moiety
  作者：Jitendra Kumar Gupta、Pramod K. Sharma、Rupesh Dudhe、Anshu Chaudhary、Avnesh Singh、P. K. Verma、Sambhu C. Mondal、Rakesh Kumar Yadav、Shivjee Kashyap

  DOI：10.1007/s00044-011-9675-4

  日期：2012.8

  A novel series of 2-amino-4-(coumarin-3-yl)-6-substituted phenyl pyrimidines (5a-h) were synthesized from 3-acetylcoumarin (3). The structures of the synthesized compounds were elucidated by I.R., H-1 NMR, C-13 NMR, and Mass spectroscopic techniques. The synthesized compounds were screened for in vivo analgesic activities at a dose of 20 mg/kg body weight (b.w). Among them, compounds 5b and 5h exhibited significant analgesic activity comparable with control as well as standard drug diclofenac sodium using acetic acid-induced writhing model.
• Coumarin-Pyrazole Linked Carbodithioates as Potential Anti-Сancer Agents: Design, Synthesis, Biological, and Molecular Docking Investigation
  作者：M. Akki、D. S. Reddy、K. S. Katagi、A. Kumar、V. Babagond、R. S. Munnolli、S. D. Joshi

  DOI：10.1134/s1070363222100231

  日期：2022.10
• Synthesis and Biological Evaluation of a Novel Series of 1,3-Dicoumarinyl-5-aryl-2-pyrazolines
  作者：Milan Čačić、Maja Molnar、Ivica Strelec

  DOI：10.3987/com-11-12196

  日期：——

  In the present paper novel 1,3,5-trisubstituted 2-pyrazolines (4a-q) were synthesized via condensation of different substituted 3-cinnamoyl-2-oxo-2H-chromenes (2a-q) with 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetohydrazide (3). Chalcones were prepared via Claisen-Schmidt condensation by refluxing 3-acetyl-2-oxo-2H-chromen (1) with corresponding aldehydes in ethanol, in the presence of piperidine. All of these compounds were characterized by means of their IR, (1)H NMR and LC/MS/MS spectroscopic data and elemental microanalysis. Chalcones and pyrazolines were screened for their antioxidant and iron chelating activity.