Gallic Acid Is The Precursor Synthesis Of Biologically Active Hydrazone Derivatives And 1,3,4 - Oxadiazole Derivatives

In order to formulate green pesticides and protential anticancer agents, we have designed and synthesized 28 compounds starting form gallic acid in five steps: etherification, esterification, hydrazidation, hydrazone formation and cyclization. These include 3,4,5-trimethoxyphenylcarbohydrazide derivatives, 2-substitued phenyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxdiazole derivatives and acetohydrazide derivatives. The structures of the new compounds were confirmed by elemental analyses, IR, ¹H NMR and ¹³C NMR spectra. At the same time, the spectroscopic properties, and the reaction conditions were systematically discussed in the thesis. It was found that the yield of hydrazone derivatives 5 was moderate when the reaction mixture was refluxed for 30 min in anhydrous ethanol. In addition, the yield of 1,3,4-oxadiazole derivatives 6 was enhanced to 3¹0% under reflux condition for 4.0 h in anhydrous ethanol.The preliminary bioassay tests showed that hydrazone derivatives 5 exhibited weak antifungal activities in vitro, however, those exhibited satisfactory antitumor activity against PC3 cell, the antiproliferation rates of 5a, 5b and 5g were 70.6%, 53.5% and 53.0% at the concentration of 1 umol/L respectively. 1,3,4-oxadiazole derivatives 6 also exhibited weak to moderate antitumor activity against PC3 cell, such as 6c possessed moderate activity with inhibition rate of 80.7% at the concentration of 10μmol/L.