Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, HR-10000 Zagreb, Croatia.
KU Leuven Department of Microbiology, Immunology and Transplantation, Rega Institute, 3000 Leuven, Belgium.
Molecules. 2023 Apr 25;28(9):3720. doi: 10.3390/molecules28093720.
Herein, we present the design and synthesis of novel -substituted benzimidazole-derived Schiff bases, and the evaluation of their antiviral, antibacterial, and antiproliferative activity. The impact on the biological activity of substituents placed at the N atom of the benzimidazole nuclei and the type of substituents attached at the phenyl ring were examined. All of the synthesized Schiff bases were evaluated in vitro for their antiviral activity against different viruses, antibacterial activity against a panel of bacterial strains, and antiproliferative activity on several human cancer cell lines, thus enabling the study of the structure-activity relationships. Some mild antiviral effects were noted, although at higher concentrations in comparison with the included reference drugs. Additionally, some derivatives showed a moderate antibacterial activity, with precursor being broadly active against most of the tested bacterial strains. Lastly, Schiff base a 4-,-diethylamino-2-hydroxy-substituted derivative bearing a phenyl ring at the N atom on the benzimidazole nuclei, displayed a strong antiproliferative activity against several cancer cell lines (IC 1.1-4.4 μM). The strongest antitumoral effect was observed towards acute myeloid leukemia (HL-60).
本文设计并合成了一系列新型取代的苯并咪唑衍生希夫碱，并评估了它们的抗病毒、抗菌和抗增殖活性。考察了苯并咪唑核氮原子上取代基的类型以及苯环上取代基的类型对生物活性的影响。所有合成的希夫碱均在体外进行了评估，以研究它们对不同病毒的抗病毒活性、对一系列细菌菌株的抗菌活性和对几种人癌细胞系的抗增殖活性，从而研究结构-活性关系。尽管与包含的参考药物相比，在较高浓度下，观察到一些温和的抗病毒作用。此外，一些衍生物表现出适度的抗菌活性，前体 对大多数测试的细菌菌株具有广泛的活性。最后，希夫碱 一个 4-，-二乙基氨基-2-羟基取代的衍生物，在苯并咪唑核的氮原子上带有一个苯环，对几种癌细胞系显示出很强的抗增殖活性（IC 1.1-4.4 μM）。在急性髓系白血病（HL-60）中观察到最强的抗肿瘤作用。
