Synthesis and Characterization of Some Heterocyclic Compounds Derived from Schiff Base and Evaluation of Their Biological Activities
DOI:
https://doi.org/10.48048/tis.2026.11951Keywords:
P-aminosulfonic, Biological activities, Schiff base, Docking study, Heterocyclic, AntibacterialAbstract
Heterocyclic compounds represent one of the most important classes in organic chemistry due to their wide range of biological and pharmacological activities. In this study, new Schiff bases were synthesized through the condensation of benzaldehyde derivatives with para-aminosulfonic acid. These intermediates were subsequently cyclized to obtain four-, five-, and seven-membered heterocyclic systems, including thiazolidine, oxazepine, and benzooxazepine derivatives. The structures of the synthesized compounds were confirmed using elemental analyses and spectral techniques (IR, ¹H-NMR, and ¹³C-NMR). The antimicrobial activity of the prepared compounds was evaluated against Gram-positive and Gram-negative bacterial strains, as well as yeast species. Results revealed that compounds 8, 10, 11, and 13 displayed notable inhibitory effects, particularly at higher concentrations, with compound 13 showing the strongest biological activity. Furthermore, molecular docking simulations demonstrated favorable binding interactions of selected compounds with the active sites of target proteins, indicating their potential as promising leads for drug development.
HIGHLIGHTS
- Novel Schiff bases and their heterocyclic derivatives (thiazolidine, oxazepine, and benzooxazepine) were successfully synthesized.
- Structural elucidation was confirmed using IR, ¹H-NMR, and ¹³C-NMR spectroscopy.
- Selected compounds exhibited significant antimicrobial activity against Gram-positive and Gram-negative bacteria.
- Compound 13 demonstrated the highest inhibitory activity in vitro.
- Molecular docking studies revealed strong hydrogen bonding and hydrophobic interactions with target proteins.
- Findings highlight Schiff base-derived heterocycles as promising scaffolds for further pharmaceutical development.
GRAPHICAL ABSTRACT
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