(2E,4Z)-5-chloro-5-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one | 1227403-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2E,4Z)-5-chloro-5-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one
• CAS: 1227403-42-0
• 化学式: C₁₉H₁₆ClFO₄
• 分子量: 362.785
• InChiKey: ZSJPCUMKXAOTBV-MUKQYHNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 β-chloro-β-(4-fluorophenyl)acrylaldehyde 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以30%的产率得到(2E,4Z)-5-chloro-5-(4-fluorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)penta-2,4-dien-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of β-chloro vinyl chalcones as inhibitors of TNF-α and IL-6 with antimicrobial activity

  摘要：

  A series of beta-chloro vinyl chalcones have been synthesized by Claisen-Schmidt condensation. beta-chloro vinyl aldehyde has been synthesized by the Vilsmayer-Hack formylation reaction. The structures of the newly synthesized compounds were confirmed by H-1 NMR, IR and Mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-alpha and IL-6) and antimicrobial (antibacterial and antifungal) activity. Compounds 5a, 5d, 5e, 5g and 5i exhibited promising activity against IL-6 with 58-83% inhibition at 10 mu M concentration None of the compound was found to be cytotoxic in CCK-8 cells at 10 mu M concentration. Whereas compounds 5b, 5d, Se and 5i showed very good antibacterial activity and compounds 5a, 5b, Se and 5i showed good antifungal activity.

  DOI：

  10.1016/j.ejmech.2010.01.050

文献信息

• Synthesis and biological evaluation of β-chloro vinyl chalcones as inhibitors of TNF-α and IL-6 with antimicrobial activity
  作者：Babasaheb P. Bandgar、Sachin A. Patil、Balaji L. Korbad、Shivraj H. Nile、Chandrahase N. Khobragade

  DOI：10.1016/j.ejmech.2010.01.050

  日期：2010.6

  A series of beta-chloro vinyl chalcones have been synthesized by Claisen-Schmidt condensation. beta-chloro vinyl aldehyde has been synthesized by the Vilsmayer-Hack formylation reaction. The structures of the newly synthesized compounds were confirmed by H-1 NMR, IR and Mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-alpha and IL-6) and antimicrobial (antibacterial and antifungal) activity. Compounds 5a, 5d, 5e, 5g and 5i exhibited promising activity against IL-6 with 58-83% inhibition at 10 mu M concentration None of the compound was found to be cytotoxic in CCK-8 cells at 10 mu M concentration. Whereas compounds 5b, 5d, Se and 5i showed very good antibacterial activity and compounds 5a, 5b, Se and 5i showed good antifungal activity.