Synthesis, Characterization And Biological Activities Of 5-aryl-2-furfuraldehyde-N-aroxyacetylhydrazones

Acylhydrazones have attracted much attention in recent twenty years because of their wide biological and pharmacological activities, strong tendency to chelate to metals with varied coordination modes, non-linear optical properties, and their applications as analytical and catalytical agents. There are lots of articles publicated on the magazines of Inorganic Chemistry, Metal-Organic Chemistry and Biological Chemistry et al. In order to search for new acylhydrazones having higher and better biological activities, we designed and synthesized fifty aroylhydrazones. Our work can be devided in three parts: The first one is the synthesis of aroylhydrazones. Five important intermediate compounds, 5-aryl-2-furfuraldehydes, were synthesized by reaction of furfuraldehyde with substituted aryldiazonium salts in acid condition. Then ten other intermediate products, aryloxyacetylhydrazines, were prepared by reaction of substituted phenols or naphthols with chloroacetic acid. By reaction of the two intermediate compounds in refluxing ethanol, fifty new target compounds, 5-aryl-2-furfuraldehyde-N-aryloxyacetylhydrazones have been synthesized. The second one is the characterization of intermediate and target compounds. By IR, 1H NMR, 13C NMR and elemental analyses, we characterized the structures of the intermediate and the target compounds. By means of D NMR and DPFGSE-NOE experiments, stereochemical behaviors of the target compounds have been studied in dimethyl-d6 sulfoxide solution. The third one is the biological activities experiments. The result of experiments is shown that the target compounds have no apparent antifungal activities on Escherichia Coli, Staphylococcus Aureus and Dysentery bacillus.