Quaternary Ammonium Salt Strategy and Molecular Docking Studies of Novel 5-Acyl-8-(Arylamino)-Quinolines by Acetyl and Methanesulfonyl Chloride for Dual Evaluation Bioactivity

Six quinoline derivatives containing quaternary ammonium salts and acyl chloride groups were synthesized from ethyl 8-chloro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate in several step. With berberine as the positive control, three human cancer cell lines (HCT-116, Hela and A549) and human normal liver L-02 cell lines were used to evaluate the cytotoxicity of the newly synthesized compounds in vitro. Compound (V–X) showed good antitumor activity, and the test result of compound (VII) was better than that of positive control group. In terms of antibacterial activity, compound (V–X) has obvious inhibitory effect on Staphylococcus aureus (ATCC 29213) and Escherichia coli (ATCC 8739), and its antibacterial activity is about 1–4 times that of positive control amoxicillin and 1–2 times that of ciprofloxacin. Among them, the most effective compounds (VII) and (X) have 4-fold the antibacterial activity of amoxicillin and 2-fold the antibacterial activity of ciprofloxacin. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1134/S1068162023020097.