3-(5-phenylpenta-2,4-dienoyl)-2H-chromen-2-one | 136261-24-0

• 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: 3-(5-phenylpenta-2,4-dienoyl)-2H-chromen-2-one
• 英文别名: 3-(5-Phenylpenta-2,4-dienoyl)chromen-2-one
• CAS: 136261-24-0
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: MAEHLJOAKVDOAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 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-(5-phenylpenta-2,4-dienoyl)-2H-chromen-2-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84%的产率得到5-styryl-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 哌啶 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 3-(5-phenylpenta-2,4-dienoyl)-2H-chromen-2-one
  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

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）。
• Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents
  作者：Suresh Khode、Veeresh Maddi、Prashant Aragade、Mahesh Palkar、Pradeep Kumar Ronad、Shivalingarao Mamledesai、A.H.M. Thippeswamy、D. Satyanarayana

  DOI：10.1016/j.ejmech.2008.09.020

  日期：2009.4

  A novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines (3a–l) were synthesized by reacting various substituted 3-aryl-1-(3-coumarinyl)propan-1-ones (2a–l) with phenylhydrazine in the presence of hot pyridine. Structures of all new synthesized compounds were characterized on the basis of elemental analysis and spectral data (IR, 1H NMR and 13C NMR). The title compounds were screened

  通过使各种取代的3-芳基-1-（3-香豆基）丙烷反应，合成了一系列新的5-（取代）芳基-3-（3-香豆基）-1-苯基-2-吡唑啉（3a - l）。在热吡啶存在下与苯肼形成1-ones（2a – l）。根据元素分析和光谱数据（IR，1 H NMR和13 C NMR）对所有新合成化合物的结构进行表征。以12 mg制备的化合物中的化合物3d，e，i和j为原料，以200 mg / kg bw的剂量筛选标题化合物的体内抗炎和镇痛活性。在角叉菜胶诱导的大鼠水肿爪等急性炎症模型中显示出显着的抗炎活性，而在3D辅助佐剂诱发的关节炎等慢性炎症模型中，化合物3d和e显示出显着的活性，并与双氯芬酸（13.5 mg / kg bw）进行了比较作为标准药物。还发现这些化合物在乙酸诱导的扭体模型中具有显着的镇痛活性，在酵母诱导的发热模型中具有最小的致溃疡指数，具有解热活性。
• Novel inhibitors of human histone deacetylases: Design, synthesis and bioactivity of 3-alkenoylcoumarines
  作者：Carole Seidel、Michael Schnekenburger、Clemens Zwergel、François Gaascht、Antonello Mai、Mario Dicato、Gilbert Kirsch、Sergio Valente、Marc Diederich

  DOI：10.1016/j.bmcl.2014.06.067

  日期：2014.8

  Histone deacetylases (HDACs) are well-established, promising targets for anticancer therapy due to their critical role in cancer development. Accordingly, an increasing number of HDAC inhibitors displaying cytotoxic effects against cancer cells have been reported. Among them, a large panel of chemical structures was described including coumarin-containing molecules. In this study, we described synthesis and biological activity of new coumarin-based derivatives as HDAC inhibitors. Among eight derivatives, three compounds showed HDAC inhibitory activities and antitumor activities against leukemia cell lines without affecting the viability of peripheral blood mononuclear cells from healthy donors.
• Co-initiator compositions for photopolymerization containing 3-acyl-substituted coumarins, photopolymerizable composition and photographic element
  申请人：EASTMAN KODAK COMPANY (a New Jersey corporation)

  公开号：EP0022188B1

  公开（公告）日：1984-10-03