سنتز ترکیبات جدید دی هیدروپیریمیدین -2-اون با پتانسیل اثر ضد میکروبی و ضد التهابی

Background and purpose: Dihydropyrimidins are bioisoester of dihydropyridine. In addition to blocking of calcium channels, they have antimicrobial, antiviral, antifungal, antiparasital and antiinflammatory activities. Monastrol is an anticancer dihydropyrimidine derivation that inhibits mitosis. Several marine alkaloids with dihydropyrimidine skeletal have been isolated. In this study, several compounds with dihydropyrimidines skeletal were prepared by reaction of imidazole aldehyde, urea and β-keto ester. Material and methods: Imidazole derivatives were synthesized by the reaction of the starting materials, methyl amine hydrochloride and dihydroxyaceton dimer with potassium thiocyanate under the reflux condition, using acetic acid and n-Butanol as solvent. In the next step, corresponding product was methylated by methyl iodide. This product was then oxidized by MnO2 to corresponding aldehyde. The reaction of aldehyde, urea and β-ketoester (methyl, ethyl, propyl and butyl acetoacetate) in the presence of Lewis acid, gave the final products. Results: The yields were 50 to 70%. The structure of all products was confirmed by analytical methods such as NMR, IR and Mass spectra. Conclusion: Changing the solvent of a reaction is one method for increasing the yield of reaction. In this study, acid acetic was used as solvent instead of ethanol. The goal of this study was to obtain the structures with antimicrobial and anti-inflammatory activities. Because of known antimicrobial and anti-inflammatory activities of imidazolering, it seems that the combination of these two nucleuses may create structures with improved activities.