Synthesis and Characterization of Some 1,4-Dihydropyridine Derivatives Substituted at Position 1 and Evaluation of Their Biological Activity

Abstract

In this study, a series of 1,4-dihydropyridine (1,4-DHP) compounds were synthesized via a one-pot direct condensation reaction of selected reactants, using iodine (I₂) as a catalyst and ethanol as the solvent. The synthesized compounds were characterized using various spectroscopic techniques, including Fourier-transform infrared spectroscopy (FT-IR), and nuclear magnetic resonance methods such as ^1H-NMR, ^13C-NMR, HSQC, and DEPT-135.

The biological activities of the synthesized compounds were evaluated, with a focus on their anticancer potential. Cytotoxicity was assessed using the MTT assay on two cancer cell lines: MDA-MB-231 and MCF-7. Among the tested compounds (IO, BNO₂, and Br), compound Br showed the highest antiproliferative activity with an IC₅₀ value of 22.93 µg/mL, while compound BNO₂ exhibited the lowest activity, with an IC₅₀ value of 148.10 µg/mL.

Additionally, the antioxidant activities of compounds IO and Br were evaluated using the DPPH radical scavenging assay. Compound IO demonstrated stronger antioxidant activity with an IC₅₀ value of 95.087 µg/mL, compared to Br, which showed lower efficacy with an IC₅₀ of 107.17 µg/mL  Furthermore, the antibacterial activity of compound BNO₂ was tested against two bacterial strains: the Gram-positive Staphylococcus aureus and the Gram-negative Escherichia coli. The results indicated that BNO₂ was effective against the Gram-positive bacteria, while it showed weaker activity against the Gram-negative strain.

DOI: https://doi.org/10.54633/2333-024-056-019