School of Pharmacy, Jiangsu University, Zhenjiang 212013, China.
College of Animal Science and Technique, Bayi Agriculture University, Daqing 163319, Heilongjiang, China.
Bioorg Chem. 2020 Jun;99:103837. doi: 10.1016/j.bioorg.2020.103837. Epub 2020 Apr 9.
A novel of quarternary amine around a quinolinium iodide combined with even number alkyl chain were prepared in a several step in moderate yield starting from malonic ester and benzo[d][1,3]dioxol-5-amine. All of the active structure compounds were identified by nuclear magnetic resonance (NMR), such as H NMR, C NMR, infrared radiation (IR), high resolution mass spectrometry (HR-MS) and Carlo Erba Instruments CHNS-O EA1108 spectra analysis. With regard to the anticancer properties, the in vitro cytotoxicity against three human cancer cell lines (A-549, Hela and SGC-7901) were evaluated. The antibacterial properties against two human bacterial strains, Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739), along with minimum inhibitory concentration (MIC) values were evaluated. The target compounds, 5-12, exhibited significant antitumor and antibacterial activity, of which compound 12 was found to be the most potent derivative with IC values of 5.18 ± 0.64, 7.62 ± 1.05, 17.59 ± 0.41, and 54.45 ± 4.88 against A-549, Hela, SGC-7901, and L-02 cells, respectively, stronger than the positive control 5-FU and MTX. Furthermore, compound 12 had the most potent inhibitory activity. The MIC of this compound against Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739) was 3.125 nmol·mL, which was smaller than that of the reference agents, amoxicillin and ciprofloxacin.
一种新型的季铵盐，其结构为喹啉鎓碘化物与偶数个烷基链结合，是通过丙二酸酯和苯并[d][1,3]二氧杂环戊烯-5-胺的多步反应，以中等产率制备的。所有活性结构化合物都通过核磁共振（NMR），如 H NMR、C NMR、红外辐射（IR）、高分辨率质谱（HR-MS）和 Carlo Erba Instruments CHNS-O EA1108 光谱分析来鉴定。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。评估了对两种人细菌株，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。目标化合物 5-12 表现出显著的抗肿瘤和抗菌活性，其中化合物 12 是最有效的衍生物，IC 值分别为 5.18 ± 0.64、7.62 ± 1.05、17.59 ± 0.41 和 54.45 ± 4.88 对 A-549、Hela、SGC-7901 和 L-02 细胞，比阳性对照 5-FU 和 MTX 更强。此外，化合物 12 具有最强的抑制活性。该化合物对大肠杆菌（ATCC 29213）和金黄色葡萄球菌（ATCC 8739）的 MIC 为 3.125 nmol·mL，小于参考药物阿莫西林和环丙沙星。
