2-Chloroquinoline-3-carbaldehyde and 2-chloro-8-methylquinoline-3-carbaldehyde derivatives were synthesized through Vilsmeier formulation of acetanilide and N-(o-tolyl)acetamide. Aromatic nucleophilic substitution reaction was used to introduce various nucleophiles in place of chlorine under different reaction conditions. The carbaldehyde group was oxidized by permanganate method and reduced with metallic sodium in methanol and ethanol. The synthesized compounds were characterized by UV-Vis, IR, and NMR. The antibacterial activity of the synthesized compounds was screened against two Gram-positive bacteria (Bacillus subtilis ATCC6633 and Staphylococcus aureus ATCC25923) and two Gram-negative bacteria (Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853). Most of the compounds displayed potent activity against two or more bacterial strains. Among them, compounds 6 and 15 showed maximum activity against Pseudomonas aeruginosa with mean inhibition zones of 9.67 ± 1.11 and 10.00 ± 0.44 mm, respectively, while ciprofloxacin showed mean inhibition zone of 8.33 ± 0.44 mm at similar concentration. On the other hand, compound 8 exhibited maximum activity against Escherichia coli with inhibition zones of about 9.00 ± 0.55 mm at 300 μg/mL and 11.33 ± 1.11 mm at 500 μg/mL. The radical scavenging activity of these compounds was evaluated using 1,1-diphenyl-2-picryl hydrazyl (DPPH), and all of them displayed moderate antioxidant activity, with compound 7 exhibiting the strongest activity. The molecular docking study of the synthesized compounds was conducted to investigate their binding pattern with DNA gyrase, all of them were found to have minimum binding energy ranging from –6.0 to –7.33 kcal/mol, and the best result was achieved with compound 11. The findings of the in vitro antibacterial and molecular docking analysis demonstrated that the synthesized compounds have potential of antibacterial activity and can be further optimized to serve as lead compounds.

中文翻译：

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一些新型喹啉衍生物的合成及抗菌、抗氧化和分子对接分析

通过乙酰苯胺和 N-(o-tolyl) 乙酰胺的 Vilsmeier 配方合成了 2-Chloroquinoline-3-carbaldehyde 和 2-chloro-8-methylquinoline-3-carbaldehyde 衍生物。芳香亲核取代反应用于在不同反应条件下引入各种亲核试剂代替氯。甲醛基团用高锰酸盐法氧化，并在甲醇和乙醇中用金属钠还原。合成的化合物通过UV-Vis、IR和NMR表征。合成化合物对两种革兰氏阳性菌（枯草芽孢杆菌 ATCC6633 和金黄色葡萄球菌 ATCC25923）和两种革兰氏阴性菌（大肠杆菌 ATCC 25922 和铜绿假单胞菌 ATCC 27853）的抗菌活性进行了筛选。大多数化合物对两种或多种细菌菌株显示出有效的活性。其中，化合物 6 和 15 对铜绿假单胞菌的活性最大，平均抑菌圈分别为 9.67 ± 1.11 和 10.00 ± 0.44 mm，而环丙沙星在相似浓度下的平均抑菌圈为 8.33 ± 0.44 mm。另一方面，化合物 8 对大肠杆菌表现出最大的活性，抑制区在 300 μg/mL 时为约 9.00 ± 0.55 mm，在 500 μg/mL 时为 11.33 ± 1.11 mm。使用1,1-二苯基-2-苦基肼(DPPH)评估这些化合物的自由基清除活性，它们都表现出中等的抗氧化活性，其中化合物7表现出最强的抗氧化活性。对合成化合物进行分子对接研究，以研究它们与 DNA 促旋酶的结合模式，