Murrayanine-Chalcone Transformed into Novel Pyrimidine Compounds Demonstrated promising Anti-Inflammatory Activity

Abstract

A new series of murrayanine based pyrimidine derivatives were synthesized from the previously reported starting material, known as murrayanine-chalcone and urea as the reagent in alkaline-ethanolic media. The in vivo anti-inflammatory activity of the fabricated compounds was performed by the carrageenan-induced paw edema standard method. The produced molecules were characterized using modern sophisticated analytical techniques such as IR, 1H-NMR, and mass spectral data, spectroscopic data revealed the possible structures of the synthesized compounds and characterization data were found to be in full agreement with that of the structures. The compound 6-(4-fluorophenyl)-4-(1-methoxy-9H-carbazol-3-yl)-1, 6-dihydropyrimidin-2-ol (3b), having para-fluorine substituent exhibited the highest anti-inflammatory activity with 58.33% reduction after 3 hrs. The anti-inflammatory activity was observed to be reasonably analogous with that of indomethacin, the standard drug. A very clear structure-activity relationship was not established due to mixed results. It was detected that fluorine substituted compound exhibited the best activity, followed by bromine, and iodine substituent. It was also seen that while substituting the chlorine along with fluorine in the derivative, the activity fallen drastically. The introduction of bulky group did not show an impressive activity as compared to the single electron-withdrawing group. On increasing the number of substituent to double, it was found that the activity reduces severely. This research will undoubtedly encourage scientists across the globe in the rational designing and synthesis of molecules with distinct pharmacological action(s).