MOLECULAR DESIGN, SYNTHESIS, CHARACTERIZATION AND ANTIBACTERIAL EVALUATION OF (2E)-1-(CYCLOHEXYL(PHENYL)METHYLENE)-2-(2-METHOXYBENZYLIDENE) HYDRAZINE

Abstract

The Schiff base derivatives have drawn a lot of interest in the field of medicinal chemistry due to their diverse biological activities and versatility in structure. In the current work, (2E)-1-(cyclohexyl(phenyl)methylene)-2-(2-methoxybenzylidene)hydrazine which is a hydrazone derivative of a Schiff base has been synthesized through condensation reaction of (Z)-(cyclohexyl(phenyl)methylene)hydrazine with 2-methoxybenzaldehyde under reflux conditions in ethanol. The product of the synthesis was obtained in 72 % yield and was obtained in the form of brown crystalline solid with a melting point of 178 ^oC. The ¹H NMR and FT-IR spectroscopic methods were used to confirm the molecular structure of the compound. The property of the synthesized compound as an antibacterial agent was tested against Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative) by the agar well diffusion technique. Ciprofloxacin was used as a positive control, whereas dimethyl sulfoxide (DMSO) served as the negative control. The compound formed had a moderate antibacterial activity with 14.0 ± 0.5 mm and 12.0 ± 0.6 mm being the inhibition zones with Staphylococcus aureus and Escherichia coli respectively. Comparatively, the standard antibiotic, ciprofloxacin, had larger areas of inhibition 26.0 ± 0.4 mm and 24.0 ± 0.5 mm, respectively, whereas the negative control did not have an antibacterial effect. The reason why the Gram-positive bacterium is slightly more susceptible to the activity could be the variation in the structural composition of bacterial cell walls. The findings indicate that the synthesized hydrazone derivative of Schiff base has good antibacterial activity and could be used as a useful scaffold in designing new biologically active compounds.