Design, synthesis, structure elucidation, and biological activities of 3-(substituted amino)-1-(pyridin-4-yl)propenones and 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidine–adamantane hybrids

Abstract

Novel molecular hybrids of 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidine–adamantane have been synthesized in excellent yields by the reaction of enaminones, 1-adamantanamine, and formaldehyde. Enaminones (Z)-3-alkyl/aralkyl/aryl-1-(pyridin-4-yl)prop-2-en-1-ones have been synthesised by the reaction of 4-acetylpyridine with N,N-dimethylformamide dimethyl acetal and its bioassay test showed good anti-inflammatory property, but no zone of growth inhibition against Bacillus subtilis (MTCC Code-121), Staphylococcus aureus (MTCC Code-9886), Escherichia coli (MTCC Code-1302), and Salmonella enterica (MTCC Code-3232) bacterial strains. The structures of the synthesized compounds have been established with the help of spectral and analytical data. X-ray analysis of a representative candidate of the series 5-isonicotinoyl-1,2,3,4-tetrahydropyrimidine–adamantane was done for the final confirmation of the structure.