Department of Chemistry, Faculty of Science, Al-Azhar University (Girls Branch), P.O. box 11754, Youssef Abbas Str., Cairo, Egypt.
Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, P. O. Box 13401, Makkah 21955, Saudi Arabia.
Anticancer Agents Med Chem. 2019;19(9):1132-1140. doi: 10.2174/1871520619666190319142934.
Quinolones are a significant group of nitrogen heterocyclic compounds that exist in therapeutic agents, alkaloids, and synthetic small molecules that have important biological activities. A wide range of quinolones have been used as antituberculosis, antibacterial, anti-malarial, antifungal, anticonvulsant, anticancer agents and urease inhibitors.
Ethyl 3,3-disubstituted-2-cyano propionates containing hybride quinolones derivatives were synthesized by the reaction of 1-amino-7-hydroxy-4-methylquinolin-2(1H)-one and its dibromo derivative with α, β-unsaturated carbonyl in ethanol.
A novel series of hybrid 2-quinolone derivatives was designed and synthesized. The compounds structures were confirmed using different spectroscopic methods and elemental analysis. The cytotoxic activities of all the compounds were assessed against HepG2 cell line in comparison with doxorubicin as a standard drug.
Most compounds revealed superior anti-proliferative activity than the standard. Compound 4b, is the most active compound (IC50 = 0.39mM) compared with doxorubicin (IC50 = 9.23mM). DNA flow cytometric analysis of compound 4b showed cell cycle arrest at G2/M phase with a concomitant increase of cells in apoptotic phase. Dual annexin-V/ propidium iodide staining assay of compound 4b revealed that the selected candidate increased the apoptosis of HepG-2 cells more than control.
喹诺酮类是一组重要的氮杂环化合物，存在于治疗剂、生物碱和合成小分子中，具有重要的生物活性。许多喹诺酮类化合物被用作抗结核、抗菌、抗疟、抗真菌、抗惊厥、抗癌药物和脲酶抑制剂。
通过 1-氨基-7-羟基-4-甲基喹啉-2（1H）-酮及其二溴衍生物与α，β-不饱和羰基在乙醇中的反应，合成了含杂合喹诺酮衍生物的 3,3-二取代-2-氰基丙酸乙酯。
设计并合成了一系列新型杂合 2-喹诺酮衍生物。通过不同的光谱方法和元素分析确认了化合物的结构。将所有化合物的细胞毒性活性与阿霉素作为标准药物进行了比较，评估了它们对 HepG2 细胞系的抑制作用。
与标准药物相比，大多数化合物表现出更强的抗增殖活性。与阿霉素（IC50 = 9.23mM）相比，化合物 4b（IC50 = 0.39mM）是最具活性的化合物。化合物 4b 的 DNA 流式细胞术分析显示细胞周期停滞在 G2/M 期，同时凋亡期的细胞增多。化合物 4b 的双 Annexin-V/碘化丙啶染色试验显示，与对照相比，所选候选药物增加了 HepG-2 细胞的凋亡。
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