SYNTHESIS, CHARACTERIZATION, AND ANTIMICROBIAL EFFECT OF BISBENZYLIDENE DERIVATIVES OF CYCLOHEXANONE AND CYCLOPENTANONE
AZIBANASAMESA DUMARO CHARLES OWABA1* , ABRAHAM SISEIN EBOH2, DARLINGTON DEBOH EBOH3, SAMUEL JACOB BUNU1, WOYENGIKURO SHEMDICKSON1, TIEMO CHARIS1, PAUL UCHENNA UGWUABOR
- Department of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmacy, Niger Delta University, Wilberforce Island, Bayelsa State, Nigeria.
- Department of Biochemistry, Faculty of Basic Medical Science, Niger Delta University, Wilberforce Island, Bayelsa State, Nigeria.
- Department of Pharmaceutical Microbiology and Biotechnology, Faculty of Pharmacy, Niger Delta University, Wilberforce Island, Bayelsa State, Nigeria.
Afr. J Pharm Res Dev; Volume 17(3): 335-349; 2025
ABSTRACT
Dibenzylidene derivatives of cyclohexanone and cyclopentanone were synthesized by reacting appropriate aromatic aldehyde, such as benzaldehyde, anisaldehyde and piperonal, to obtain dibenzylidene derivatives of cyclohexanone and cyclopentanone using the Claisen-Schmidt condensation reaction. The reaction was catalysed with 30% sodium hydroxide solution at 0-10°C and was kept in the refrigerator for 7 days. The progress of the reaction was monitored using TLC in a solvent system (Ethyl acetate: Methanol 1:1), and thereafter treated with acetic acid and the precipitates collected, dried and recrystallized in methylated spirit, filtered and dried. The yield, melting point and spectral analysis were determined. The antimicrobial assay was carried out using the broth dilution method at 512, 256, 128, 64, 32, 16, 8, 4, 2, and 1µg/mL against S. aureus, Escherichia spp., Bacillus spp, Klebsiella spp. and Candida albicans. The yield of the compounds ranges (50.3-99%), the melting point ranges (108-246°C) and the spectral analyses conformed as projected. This was revealed by 1H, 13C-NMR, and HRMS (ESI) data. The compounds had no antibacterial effect at the concentration assessed.
Keywords: Dibenzylidene, Antimicrobial, Spectral analyses, Cyclohexanone, Cyclopentanone
Email of correspondence: azibanasamesa@gmail.com
https://doi.org/10.59493/ajopred/2025.3.10 ISSN: 0794-800X (print); 1596-2431 (online)