The Synthesis And Characterization Of Flavone-6-carboxylic Acid Derivatives

Flavonoids are compounds full of biological activities which attract many scientists for more than one hundred years. To synthesize new falconoid with more activities and less toxicity is a hot topic of many organic chemists and pharmacy jurists. In this thesis, we have selected the flavonoid as the target, synthesized, characterized a series of flavone-6-carboxylic acid and optimized the reaction conditions.There are many kinds of supramolecular forces in the crystal structure of falconoid, including the interactions of the molecular, the actions between the groups of the same molecular, concerning the structures and characters of many kinds of supramolecular, molecular assemblies and molecular aggregates, involving the interaction of life substance etc. The studies on the crystal structure and supramolecular forces of the flavonoid will play an important role in the deeper studies of the structure-activity relation and pharmacological mechanism. In this thesis, the crystal structure and supramolecular forces of several flavone-6-carboxylic acid have been studied.Our work was carried out as follows:Firstly, the recent progress of the biological activities, synthesis, and structure-activity relationship of the flavones has been reviewed extensively based on the detailed investigation of related literatures.Secondly, the effects of different phase transfer catalysts on the synthesis of chalcone in water were studied and four chalcones compounds were synthesized. 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 acid in conditions of microwave radiation and I2/DMSO as the oxidant was studied, eight flavone-6-carboxylic acid compounds were synthesized and their reaction conditions were optimized. Their structures were characterized by IR, H-NMR and MS (ESI). Two 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, four crystals of the flavone-6-carboxylic acid derivatives were obtained and their crystal structures were detected by the single crystal X-ray diffraction. Their crystal structure and supramolecular forces were studied for the first time which provided theoretical basis for the further studies on the structure-activity relation and pharmacological mechanism.