A class of 2-(1-imidazol-1-yl)-1-phenylethyl cinnamates and 2-(1-benzo[]imidazol-1-yl)-1-phenylethyl cinnamates were synthesized, and their synthesis was validated using various spectroscopic techniques like IR, NMR, and Mass spectrometry. In addition, the compounds were assessed for antibacterial against gram-positive and gram-negative strains and antifungal against six different fungal strains. Compounds , , , and exhibited significant activity against all bacterial strains ranging from and compounds , , and exhibited considerable activity against all fungal strains ranging from . A molecular docking study indicated that compounds and could be lodged in the active pocket and inhibit Sterol 14α-demethylase (CYP51) protein via various interactions, and these studies validate the antifungal results. Different parameters from the 100 ns MD simulation study are investigated to evaluate the dynamic stability of protein-ligand complexes. According to the MD simulation study, the proposed compounds effectively kept their molecular interaction and structural integrity within the Sterol 14-demethylase. Compounds , , and are promising lead compounds in searching for novel antifungal drug-like molecules. Furthermore, ADME indicates that these compounds possess drug-like physicochemical properties to be orally bioavailable.Communicated by Ramaswamy H. Sarma.