The Synthesis And Characterization Of Flavone-8-Carboxylic Acid Derivatives

Flavonoids are compounds full of biological activities and special plastic structure, and the toxicity is extremely small which attract many scientists for more than one hundred years. To synthesize falconoid and modify structure is a hot topic of many organic chemists and pharmacy jurists. The carboxyl is introduced to matrix of falconoid which can increase the active is a hot research topic in this field. In this thesis, we have selected the flavone carboxylic acids as the target, synthesized, characterized a series of flavone-8-carboxylic acid and optimized the reaction conditions.This paper was carried out as follows:Firstly, the recent progress of the biological activities, synthesis, and structure-activity relationship of the flavone carboxylic acids has been reviewed extensively based on the detailed investigation of related literatures.Secondly, it was studied about the effects on synthesis reaction of different solvents, ratio of reactants, the dosage and concentration of alkali and four chalcones compounds were synthesized, three of them were new compounds which haven't been reported. Their reaction conditions were optimized too. This synthetic route provided a direction for the research of synthesizing chalcone in a green, environmental protection method.Thirdly, the synthesis of flavone carboxylic acids in conditions of microwave radiation and I₂/DMSO as the oxidant was studied, eight flavone-8-carboxylic acid compounds were synthesized and their reaction conditions were optimized. Their structures were characterized by IR, H-NMR and MS (ESI). Seven of them were new compounds which haven't been reported. Advantages of this method are short reaction time, simple reaction process and high yield.Fourthly, one crystals of the flavone-8-carboxylic acid derivatives were obtained and their crystal structures were detected by the single crystal X-ray diffraction. Their crystal structure was studied for the first time which provided theoretical basis for the further studies on the structure-activity relation and pharmacological mechanism.