Synthesis and biological profiling of novel pyrazoles as antioxidant, antibacterial, and antimitotic agents: An <i>in vitro</i> and <i>in silico</i> approach

In this study, we report the synthesis and comprehensive characterization of a novel series of two Ethyl 3-Aryl-2-cyano-3-(3-hydroxy-5-methyl-1H-pyrazol-4-yl) propanoate derivatives
3a
and
3b
. The structural elucidation of these compounds was carried out using nuclear magnetic resonance (
1
H &amp;
13
C)-(NMR) spectroscopy and mass spectrometry. This study investigated the biological activities of two synthesized pyrazole derivatives, compounds
3a
and
3b
. Both showed moderate, dose-dependent antioxidant activity in the DPPH assay, with compound
3a
exhibiting slightly better potency (IC
50
= 0.98 µmol/mL). Antibacterial evaluations revealed that compound
3b
displayed strong activity against
Staphylococcus aureus
(inhibition zone: 18.9 mm; MIC = 1.25 µmol/mL), while compound
3a
showed limited efficacy, especially against Gram-negative strains. In antimitotic assays, compound
3a
demonstrated a moderate antigermination effect (20% inhibition), compared with 10% for compound
3b
, consistent with their respective mitotic index results. Molecular docking studies revealed that both compounds
3a
and
3b
exhibit strong binding affinities toward antioxidant (Keap1), antibacterial (DNA gyrase), and antimitotic (tubulin) targets. Notably,
3a
consistently showed superior interaction profiles, suggesting higher bioactivity potential across all targets. The binding stability of compound
3a
with DNA gyrase and tubulin was further investigated and validated through molecular dynamics simulations. These findings suggest promising antioxidant and antibacterial potential, particularly for compound
3b
, and notable antimitotic activity for compound
3a
.