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Design, Synthesis, and Dual Evaluation of Quinoline and Quinolinium Iodide Salt Derivatives as Potential Anticancer and Antibacterial Agents
Author(s) -
Jin Guofan,
Xiao Fuyan,
Li Zhenwang,
Qi Xueyong,
Zhao Lei,
Sun Xianyu
Publication year - 2020
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.202000002
Subject(s) - hela , quinoline , chemistry , antibacterial activity , escherichia coli , staphylococcus aureus , ciprofloxacin , minimum inhibitory concentration , in vitro , iodide , stereochemistry , antibacterial agent , combinatorial chemistry , antibiotics , bacteria , biochemistry , organic chemistry , biology , gene , genetics
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 IC 50 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.