Design, Synthesis, and Dual Evaluation of Quinoline and Quinolinium Iodide Salt Derivatives as Potential Anticancer and Antibacterial Agents

A series of novel quinoline and quinolinium iodide derivatives were designed and synthesized to discover potential anticancer and antibacterial agents. With regard to anticancer properties, in vitro cytotoxicities against three human cancer cell lines (A‐549, HeLa and SGC‐7901) were evaluated. The antibacterial properties against two strains, Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739), along with minimum inhibitory concentration (MIC) values were evaluated. The target alkyliodine substituted compounds exhibited significant antitumor and antibacterial activity, of which compound 8‐((4‐(benzyloxy)phenyl)amino)‐7‐(ethoxycarbonyl)‐5‐propyl‐[1,3]dioxolo[4,5‐g]quinolin‐5‐ium (12) was found to be the most potent derivative with IC50 values of 4.45±0.88, 4.74±0.42, 14.54±1.96, and 32.12±3.66 against A‐549, HeLa, SGC‐7901, and L‐02 cells, respectively, stronger than the positive controls 5‐FU and MTX. Furthermore, compound 12 had the most potent bacterial inhibitory activity. The MIC of this compound against both E. coli and S. aureus was 3.125 nmol ⋅ mL−1, which was smaller than that against the reference agents amoxicillin and ciprofloxacin. Double function: A series of quinoline and quinolinium iodide derivatives were synthesized starting from ethyl 8‐chloro‐[1,3]dioxolo[4,5‐g]quinoline‐7‐carboxylate and the arylamine compounds to discover potential anticancer and antibacterial agents. The target compound 12 was found to be the most potent derivative with IC50 values lower than those of the positive controls 5‐fluorouracil and methotrexate. Furthermore, compound 12 had the most potent inhibitory activity; its MIC value against test cells was 3.125 nmol mL−1, which was smaller than those of the reference agents amoxicillin and ciprofloxacin.