(E)-3-(2,4-dimethoxyphenyl)-1-(4-pyrrol-1-ylphenyl)prop-2-en-1-one | 1393645-56-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(2,4-dimethoxyphenyl)-1-(4-pyrrol-1-ylphenyl)prop-2-en-1-one
• CAS: 1393645-56-1
• 化学式: C₂₁H₁₉NO₃
• 分子量: 333.387
• InChiKey: OEDSKRWQKOWNKI-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氟苯乙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (E)-3-(2,4-dimethoxyphenyl)-1-(4-pyrrol-1-ylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Antimalarial Activity of Newly Synthesized Chalcone Derivatives In Vitro

  摘要：

  Twenty‐seven novel chalcone derivatives were synthesized using Claisen‐Schmidt condensation and their antimalarial activity against asexual blood stages of Plasmodium falciparum was determined. Antiplasmodial IC50 (half‐maximal inhibitory concentration) activity of a compound against malaria parasites in vitro provides a good first screen for identifying the antimalarial potential of the compound. The most active compound was 1‐(4‐benzimidazol‐1‐yl‐phenyl)‐3‐(2, 4‐dimethoxy‐phenyl)‐propen‐1‐one with IC50 of 1.1 μg/mL, while that of the natural phytochemical, licochalcone A is 1.43 μg/mL. The presence of methoxy groups at position 2 and 4 in chalcone derivatives appeared to be favorable for antimalarial activity as compared to other methoxy‐substituted chalcones. Furthermore, 3, 4, 5‐trimethoxy groups on chalcone derivative probably cause steric hindrance in binding to the active site of cysteine protease enzyme, explaining the relative lower inhibitory activity.

  DOI：

  10.1111/j.1747-0285.2012.01383.x

文献信息

• Antimalarial Activity of Newly Synthesized Chalcone Derivatives In Vitro
  作者：Neesha Yadav、Sandeep K. Dixit、Amit Bhattacharya、Lokesh C. Mishra、Manish Sharma、Satish K. Awasthi、Virendra K. Bhasin

  DOI：10.1111/j.1747-0285.2012.01383.x

  日期：2012.8

  Twenty‐seven novel chalcone derivatives were synthesized using Claisen‐Schmidt condensation and their antimalarial activity against asexual blood stages of Plasmodium falciparum was determined. Antiplasmodial IC50 (half‐maximal inhibitory concentration) activity of a compound against malaria parasites in vitro provides a good first screen for identifying the antimalarial potential of the compound. The most active compound was 1‐(4‐benzimidazol‐1‐yl‐phenyl)‐3‐(2, 4‐dimethoxy‐phenyl)‐propen‐1‐one with IC50 of 1.1 μg/mL, while that of the natural phytochemical, licochalcone A is 1.43 μg/mL. The presence of methoxy groups at position 2 and 4 in chalcone derivatives appeared to be favorable for antimalarial activity as compared to other methoxy‐substituted chalcones. Furthermore, 3, 4, 5‐trimethoxy groups on chalcone derivative probably cause steric hindrance in binding to the active site of cysteine protease enzyme, explaining the relative lower inhibitory activity.