3-(3-methoxyphenyl)-1-(coumarin-3-yl)prop-2-en-1-one | 193619-93-1

• 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-methoxyphenyl)-1-(coumarin-3-yl)prop-2-en-1-one
• 英文别名: 3-[3-(3-methoxyphenyl)-acryloyl]-chromen-2-one；3-[3-(3-Methoxyphenyl)acryloyl]-2H-1-benzopyran-2-one；3-[3-(3-methoxyphenyl)prop-2-enoyl]chromen-2-one
• CAS: 193619-93-1
• 化学式: C₁₉H₁₄O₄
• mdl: MFCD15083075
• 分子量: 306.318
• InChiKey: ORMOJKBEOIPSTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-methoxyphenyl)-1-(coumarin-3-yl)prop-2-en-1-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 9.0h， 以69.59%的产率得到3-[3-(3-methoxyphenyl)-isoxazole-5-yl]-chromen-2-one
  参考文献：
  名称：

  3－2－2－2－烯基色铬2－1杂芳族衍生物的合成，表征及其作为抗炎剂的潜力

  摘要：

  通过使3- [3-（4-氯苯基）丙烯酰基] chromen-2-one和3- [3]反应合成了一系列新的含吡唑，异恶唑，恶嗪和噻嗪取代基的chromen-2-one -（3-甲氧基-苯基）-丙烯酰基] -chromen-2-one与各种环化剂，例如肼，苯肼，尿素和硫脲。所有合成化合物的结构均通过红外光谱确证，1H-NMR，质谱和元素分析数据。在角叉菜胶诱导的大鼠爪水肿模型中，以100 mg / kg体重的剂量评估了所有新合成的化合物的抗炎活性。整个系列化合物均表现出中度至良好的抗炎活性，对参比药物布洛芬（100 mg / kg）的水肿形成抑制百分比范围为39.99至63.15，在第三小时显示出78.96％的抑制作用。化合物3a，3c和3d表现出良好的抑制活性，而化合物3b，3e，3f和3j在第三小时表现出中等抑制活性。

  DOI：

  10.1002/jhet.1772
• 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-(3-methoxyphenyl)-1-(coumarin-3-yl)prop-2-en-1-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 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。
• 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。
• 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.
• 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.
• Synthesis and Characterization of Some Heteroaromatic Derivatives of 3-But-2-enoyl-chromen-2-one and Their Potential as Anti-inflammatory Agents
  作者：Priyanka Dixit、Avinash C. Tripathi、Shailendra K. Saraf

  DOI：10.1002/jhet.1772

  日期：2013.11

  mass spectroscopy, and elemental analysis data. All the newly synthesized compounds were evaluated for their anti‐inflammatory activity at a dose of 100 mg/kg body weight in carrageenan‐induced rat paw edema model. The entire series of the compounds exhibited moderate to good anti‐inflammatory activity, with the percentage inhibition of edema formation ranging from 39.99 to 63.15 against the reference

  通过使3- [3-（4-氯苯基）丙烯酰基] chromen-2-one和3- [3]反应合成了一系列新的含吡唑，异恶唑，恶嗪和噻嗪取代基的chromen-2-one -（3-甲氧基-苯基）-丙烯酰基] -chromen-2-one与各种环化剂，例如肼，苯肼，尿素和硫脲。所有合成化合物的结构均通过红外光谱确证，1H-NMR，质谱和元素分析数据。在角叉菜胶诱导的大鼠爪水肿模型中，以100 mg / kg体重的剂量评估了所有新合成的化合物的抗炎活性。整个系列化合物均表现出中度至良好的抗炎活性，对参比药物布洛芬（100 mg / kg）的水肿形成抑制百分比范围为39.99至63.15，在第三小时显示出78.96％的抑制作用。化合物3a，3c和3d表现出良好的抑制活性，而化合物3b，3e，3f和3j在第三小时表现出中等抑制活性。