Synthesis, Characterization and Molecular Modeling of Pyrazole-Quinoline Hybrids as New Class of Antibacterial, Antimicrobial, Anticancer Agents and DFT Study

Abstract

A new series of pyrazole-quinoline hybrids were synthesized by a base-catalyzed cyclocondensation reaction through one-pot multi-component reaction, based on molecular hybridization techniques. All the compounds 10a-x were examined for in vitro antibacterial and anticancer activities. Enzyme inhibitory activities were carried out against FabH and EGFR. From the studied compounds, most of the compounds showed effective antibacterial as well as anticancer activity against used strains and cancer cell lines, respectively. The most potent inhibitory activity was displayed by compound 10r against EGFR and by compound 10i against FabH. Spatial arrangement of the molecule and their HOMO-LUMO was studied and explained by DFT theory, to evaluate plane angle respective to the core and substitutions. Docking studies indicated that compound 10r was bound to the active pocket of EGFR with hydrogen bond and π-H interaction with minimum binding energy and compound 10i was bound to the active site of FabH with hydrogen bond and π-H interaction having minimum binding energy. Based on their substitutions, the hypothetical plane arising in the molecule and their twist angles were related with their activities against EGFR and FabH as well as antibacterial and anticancer activities.