To discover novel and effective potential anticancer agents, a series of azophenol derivatives containing 1,3,4-oxadiazoles moiety was synthesized and investigated for their anticancer activities against several human cancer cell lines by MTT method. Their structures were characterized by H NMR, C NMR, IR and HRMS spectral analyses. Among the prepared compounds, displayed significant anti-proliferative activity against HCT116 cancer cells with an IC value of 4.09 ± 0.04 µM. Moreover, this compound had low cytotoxicity against normal cells. Flow cytometric analysis indicated that compound arrested the cell cycle at S phase and induced apoptosis in a dose-dependent manner. Additionally, network pharmacology analysis calculated that might target several key proteins, including AKT serine/threonine kinase 1 (AKT1), SRC proto-oncogene, non-receptor tyrosine kinase (SRC). Furthermore, molecular docking study indicated that exhibited potentially high binding affinity to these target proteins with binding energies lower than −8 kcal/mol. These findings provide valuable insights for the development of azophenol derivatives as potential anticancer agents.

中文翻译：

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1,3,4-恶二唑氮杂酚类抗癌药物的合成、生物学评价和网络药理学研究


为了发现新型有效的潜在抗癌药物，合成了一系列含有1,3,4-恶二唑部分的偶氮酚衍生物，并通过MTT方法研究了它们对几种人类癌细胞系的抗癌活性。通过 1H NMR、13C NMR、IR 和 HRMS 光谱分析对其结构进行了表征。在制备的化合物中，对 HCT116 癌细胞表现出显着的抗增殖活性，IC 值为 4.09 ± 0.04 µM。此外，该化合物对正常细胞具有较低的细胞毒性。流式细胞术分析表明，该化合物将细胞周期阻滞在S期，并以剂量​​依赖性方式诱导细胞凋亡。此外，网络药理学分析计算出可能针对几种关键蛋白，包括 AKT 丝氨酸/苏氨酸激酶 1 (AKT1)、SRC 原癌基因、非受体酪氨酸激酶 (SRC)。此外，分子对接研究表明，其与这些靶蛋白具有潜在的高结合亲和力，结合能低于-8 kcal/mol。这些发现为偶氮酚衍生物作为潜在抗癌药物的开发提供了宝贵的见解。