5-chloro-5-(3-chlorophenyl)-1-(4-methoxyphenyl)-penta-2,4-dien-1-one | 1224257-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-5-(3-chlorophenyl)-1-(4-methoxyphenyl)-penta-2,4-dien-1-one
• 英文别名: 5-chloro-5-(3-chlorophenyl)-1-(4-methoxyphenyl)penta-2,4-dien-1-one
• CAS: 1224257-82-2
• 化学式: C₁₈H₁₄Cl₂O₂
• 分子量: 333.214
• InChiKey: VPTAWQMRFLQBSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-(3-chlorophenyl)-3-chloropropenal 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以64%的产率得到5-chloro-5-(3-chlorophenyl)-1-(4-methoxyphenyl)-penta-2,4-dien-1-one
  参考文献：
  名称：

  Synthesis and biological screening of a combinatorial library of β-chlorovinyl chalcones as anticancer, anti-inflammatory and antimicrobial agents

  摘要：

  A combinatorial library of beta-chlorovinyl chalcones ( 4) were synthesized by Claisen-Schmidt condensation reaction. Catalytic reaction of substituted 3-chloro-3-phenyl-propenal ( 2) and 1-(2,4-dimethoxyphenyl)-ethanone or 1-(4-methoxy-phenyl)-ethanone ( 3) in alkaline conditions furnished the target compound 5-chloro-1-(2,4-dimethoxy-phenyl)-5-phenyl-penta-2,4-dien-1-one ( 4). The synthesized compounds were screened for their biological activity viz. anticancer, anti-inflammatory and antimicrobial activities. Synthesized compounds 4g and 4h revealed promising anti-inflammatory activity (66-67% TNF-alpha and 95-97% IL-6 inhibitory activity at 10 mu M). Cytotoxicity of the compounds checked using CCK-8 cell lines and found to be nontoxic to slightly toxic. Furthermore, the anticancer activity (30-40%) was shown by compounds 4d, 4e, 4h and 4b at 10 mu M concentrations against ACHN followed by Calu 1, Panc1, HCT116 and H460 cell lines. Some of the compounds 4d, 4e, 4a, 4i and 4b revealed promising antimicrobial activity at MIC 50-100 mu g/mL against selected pathogenic bacteria and fungi. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.12.077