Antiproliferative properties and structural analysis of newly synthesized Schiff bases bearing pyrazole derivatives and molecular docking studies

New pyrazole Schiffbases containing azo groups were synthesized using the condensation reaction between p-nitrobenzaldehyde and (E)-4-(phenyl)-1-H-pyrazole-3,5-diamine in the molar ratio of 1:2. Characterization of the compounds was performed by spectroscopic techniques, including IR, UV-Vis, H-1-NMR and C-13-NMR. Biological activity of the compounds was evaluated by analyzing DNA protection, antimicrobial and anticancer properties. Compound 4 was effective for Salmonella typhimurium with the MIC concentration of 62.5 mu g/mL. Moreover, this compound had the highest protection activity on DNA. Cytotoxic activity of compound 4 was determined on the HeLa cancer cell line with the IC50 concentration of 976.6 mu M. The anti-cancer characteristic of compounds 4 and 5 for HeLa cancer was theoretically analyzed by molecular docking study as well. Among the tested compounds, compound 4 possessed significant results due to its in vitro cytotoxic properties. Therefore, it may be considered as a potential bioactive agent for cancer treatment studies. In addition, further in vivo analysis can be performed to indicate its anticancer property. (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

New pyrazole Schiffbases containing azo groups were synthesized and characterized by various spectroscopic techniques. Compound 4 showed significant antimicrobial activity against Salmonella typhimurium, high protection activity on DNA, and cytotoxic activity on HeLa cancer cells. The anti-cancer properties of compounds 4 and 5 were also analyzed through molecular docking study, with compound 4 exhibiting promising results in vitro.