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- Title
4′-氯-7-\[2-(哌嗪-l-基)乙氧基\]异黄酮的合成及分析方法的建立.
- Authors
连孟强; 刘娅琛; 郭春燕
- Abstract
In order to solve the problem of insufficient antitumor activity of natural daidzein (DAI),the 4 'and 7 positions of DAI were modified. Firstly, 3-(4-chlorophenyl)-7-hydroxy-4H-chromen-4-one was prepared from resorcinol and p-chlorophenylacetic acid by friedel crafts acylation, carbonization and ring closing reaction. The 3-(4-chlorophenyl)-7-\[2-(piperazin-l-yl)ethoxy\]-4H-chrome-4-one (CPEO-43) was synthesized by substitution reaction of 3-(4-Chlorophenyl)-7-hydroxy-4H-chromen-4-one with dibromoethane and piperazine. Column chromatography was used to separate the target product from impurities. Secondly, FT-IR, ¹H-NMR, 13C-NMR and MS were used to identify the compounds. Thirdly, MTT assay was used to detect the inhibitory effect of compound CPEO-43 on A549 lung cancer cells and HCT116 colon cancer cells. Finally, an ultra high performance liquid chromatography (UPLC) method was established for the analysis of CPEO-43 plasma samples.The results show that the structure of the synthesized compound is consistent with that of the target compound confirmed by FT-IR,MS,¹H-NMR and 13C-NMR. The inhibitory rates of DAI (10 μmol/L) on A549 lung cancer and HCT116 colon cancer cells are 4.421% and 5.601%, respectively. The inhibitory rates of the same concentration of CPEO-43 on A549 lung cancer cells and HCT116 colon cancer cells are 58.43% and 72.03%,respectively. The IC50 values of CPEO-43 are 2.51 μmol/L and 0.87 μmol/L,respectively. The established UPLC method has no interference from endogenous substances. The linear relationship is good in the range of 0.5~10 μg/mL. The intra-day precision and inter-day precision are less than 10%. The average recoveries of low, medium and high plasma samples of compound CPEO-43 are in the range of 92.98%~100.1%. The antitumor activity of compound CPEO-43 is significantly higher than that of DAI. The established UPLC assay method can easily and rapidly determine the content of CPEO-43 in plasma, and the results are accurate and reliable,provide a theoretical basis for improving the antitumor activity of DAI, and provide method basis for drug clinical testing.
- Publication
Journal of Hebei University of Science & Technology, 2022, Vol 43, Issue 3, p300
- ISSN
1008-1542
- Publication type
Academic Journal
- DOI
10.7535/hbkd.2022yx03010