Synthesis, Characterization, DNA Binding, Anticancer, and Molecular Docking Studies of Novel Imidazolium-Based Ionic Liquids with Fluorinated Phenylacetamide Tethers

Abstract

Newer imidazolium ionic liquid (IL) halides <b>4a-f</b> appending variety of fluorinated phenylacetamide side chains were designed and synthesized through quaternization of 1-methyl and/or 1,2-dimethylimidazole with appropriate 2-chloro-<i>N</i>-(fluorinatedphenyl)acetamides. The resulting ILs were converted to their respective ionic liquid analogues carrying fluorinated counteranions (PF₆ ^-, BF₄ ^-, and/or CF₃COO^-) <b>5a-r</b>. All newly synthesized ILs were fully characterized using several spectroscopic experiments such as ¹H, ¹³C, ¹¹B, ¹⁹F, ³¹P NMR, and mass analysis. The synthesized ionic liquids were investigated for their DNA binding and anticancer activities. The obtained DNA binding constants ranged from 1.444 × 10⁵ to 3.518 × 10⁵, indicating a reasonably good binding affinity. The percentage of anticancer activities ranged from 48 to 59 with H-1229 cell line, showing quite good anticancer potential. The modeling studies indicated the interactions of the reported molecules with DNA <i>via</i> hydrogen bonds. These were in agreement with those of DNA binding and anticancer results. Briefly, the designed ionic liquids may be used as good anticancer candidates for treating human cancer.