School of Pharmacy, Jiangsu University, Zhenjiang, 212013, China.
College of Animal Science and Technique, Bayi Agriculture University, Daqing, 163319, Heilongjiang, China.
ChemMedChem. 2020 Apr 3;15(7):600-609. doi: 10.1002/cmdc.202000002. Epub 2020 Mar 2.
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 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 , which was smaller than that against the reference agents amoxicillin and ciprofloxacin.
一系列新型的喹啉和碘化喹啉衍生物被设计和合成，以发现潜在的抗癌和抗菌药物。关于抗癌特性，评估了对三种人癌细胞系（A-549、HeLa 和 SGC-7901）的体外细胞毒性。评估了对两种菌株大肠杆菌（ATCC 29213）和金黄色葡萄球菌（ATCC 8739）的抗菌特性以及最小抑菌浓度（MIC）值。目标烷基碘取代化合物表现出显著的抗肿瘤和抗菌活性，其中化合物 8-((4-(苯甲氧基)苯基)氨基)-7-(乙氧羰基)-5-丙基-[1,3]二氧杂环[4,5-g]喹啉-5- 离子（12）是最有效的衍生物，IC 值分别为 4.45±0.88、4.74±0.42、14.54±1.96 和 32.12±3.66 对 A-549、HeLa、SGC-7901 和 L-02 细胞，均强于阳性对照 5-FU 和 MTX。此外，化合物 12 具有最强的抑菌活性。该化合物对大肠杆菌和金黄色葡萄球菌的 MIC 均为 3.125 nmol⋅mL-1，小于对照药物阿莫西林和环丙沙星。
