Synthesis And Property Study Of Chalcone Analogs

Having 1,3-diphenylacrylketone as their fundamentally skeletonized structures, Chalcones possess varieties of biological activities. In the anti-tumor, anti-inflammatory, antioxidant, antithrombotic, anti-platelet aggregation, biological activity has made rapid development. Belonging to the same kind of liquorice flavones, dibenzoylmethanes have similar chemical structures with chalones. In addition, it is of great significance for the synthesis of chalcone analogs in that dibenzoylmethanes have been widely recognized as UV absorbers with higher security so far.(1) By means of the orthogonal experiment, p-hydroxy methyl benzoate was synthesized using p-hydroxy benzoic acid as starting material and p-toluenesulfonic acid being cheap as well as easily obtained as catalyst under microwave irradiation and the optimal condition of the synthesis of objective compounds was investigated as well. The experimental results indicate that upon the conditions of the use of p-toluenesulfonic acid as catalyst, the molar ratio of alcohol, acid and catalyst being 6:1:0.12, the reaction time being 30min and irradiation power of microwave being 205W optimized by orthogonal design, the yield of the corresponding reaction could reach above 82%.(2) p-methoxy methyl benzoate was synthesized using p-hydroxy methyl benzoate as starting material, acetone as solvent and potassium carbonate as catalyst. Taking advantage of the single factor test of orthogonal method, the optimal reacting conditions of etherification having been investigated included using 0.0125mol of p-methoxy methyl benzoate, 60ml of acetone as solvent, maintaining the reaction temperature as well as time at 40℃and 4h respectively and choosing the molar ratio of p-hydroxy methyl benzoate, dimethyl sulfate and potassium carbonate being 1:3.5:4.0, which made the yield reach 94.28%. 3) 3,4,5-trimethoxymethyl benzoate was synthesized in one step using gallic acid as starting material. The optimal experimental conditions included using 0.01mol of gallic acid, toluene as solvent with a volume of 80 ml, maintaining the reaction temperature at 110℃and reaction time at 4h respectively and choosing the molar ratio of gallic acid, dimethyl sulfate and potassium carbonate being 1:16:16. This reaction of which the yield could reach 80.21% owned the advantage of simplicity as well as security.(4) Seven dibenzoylmethane compounds were synthesized from aromatic ketone and ester by classical Claisen condensation usingstrong alkali as catalyst.The sythesis of compound(4,4/-dimethoxy dibenzoylmethane)were mainly studied. The factors of condensation were investigated. The structure of products were confirmed by IR and 1HNMR.In this paper, UV-Vis spectra of seven objective compounds was determined, from which it could be concluded that all the compounds could be used as excellent UV absorbers because of their desirable UV absorbing abilities. Besides, owing to the extremely extensive pharmacological activities of chalcones, further researches should be conducted on the pharmacological actions of chalcone analogs in search for leading compounds of anticancer drugs.