Synthesis and Biological Activity of Novel Imidazole Based Chalcone Derivatives.

Abstract

Aim: To synthesize novel imidazole-based chalcone derivatives and assess their biological activities for potential drug development.

Method: The novel imidazole-based chalcone derivatives were synthesized by reacting benzylamine, dihydroxyacetone, and potassium thiocyanate, forming (1-benzyl-2-mercapto-1H-imidazol-5-yl) methanol. The introduction of methyl or ethyl iodide, coupled with oxidation using magnesium dioxide, yielded the target compounds by alkylation and oxidation method. Claisen-Schmidt condensation with various acetophenones under methanolic sodium hydroxide facilitated further derivatization. Structural elucidation involved Spectroscopic analysis and mass spectrometry, followed by antimicrobial activity testing.

Results: Compounds (9a-9j’) demonstrated varied antibacterial efficacy. Compound 9b exhibited notable activity against B. cereus and E. coli (MIC 125 µg/mL and 62.5 µg/mL). Compound 9e showed significant antibacterial activity across strains (MIC 50-125 µg/mL), and 9c consistently inhibited S. aureus, B. cereus, and P. aeruginosa (MIC 250 µg/mL). Compounds 9g and 9j’ displayed diverse antibacterial effects, indicating potential selectivity.

Conclusions: In conclusion, the synthesized imidazole-based chalcone derivatives exhibit promising antimicrobial potential, supported by methodological alignment and consistent observations in antibacterial and antifungal activities. The innovative inclusion of oxidation steps enhances structural diversity, emphasizing their efficacy against bacterial and fungal infections.