Sokol Ivana, Rakas Anja, Kučić Grgić Dajana, Persoons Leentje, Daelemans Dirk, Gazivoda Kraljević Tatjana
Department of Organic Chemistry, University of Zagreb Faculty of Chemical Engineering and Technology Marulićev trg 20 10000 Zagreb Croatia
Department of Industrial Ecology, University of Zagreb Faculty of Chemical Engineering and Technology Marulićev trg 19 10000 Zagreb Croatia.
RSC Med Chem. 2025 Apr 30. doi: 10.1039/d5md00106d.
This paper describes ultrasound synthesis, structural characterization and biological activity of new derivatives of 2-arylbenzimidazole 12-27 and 1,2,3-triazole derivatives of 2-arylbenzimidazole 28-33. The tautomeric structures of the prepared target compounds were confirmed by H- and C-NMR spectroscopy as well as by two-dimensional NOESY, HSQC and HMBC methods. The synthesized compounds underwent antiproliferative assays, revealing that compound 23 exhibited the highest potency against chronic myeloid leukemia cells (K-562, IC = 2.0 μM) and non-Hodgkin's lymphoma cells (Z-138, IC = 2.0 μM). Compound 23 was further evaluated for cytotoxicity on normal peripheral blood mononuclear cells (PBMC), and its mechanism of action was investigated. The antibacterial properties of the synthesized compounds were assessed against both Gram-positive and Gram-negative bacterial strains. Derivatives 15-17 exhibited significant selective antibacterial activity against the Gram-positive bacterium (MIC = 0.25-1 μg mL). Additionally, among the 1,2,3-triazole derivatives of 2-arylbenzimidazole, compounds 28 and 30 demonstrated strong selective activity against (MIC = 0.25 μg mL).
本文描述了2-芳基苯并咪唑12 - 27的新衍生物以及2-芳基苯并咪唑1,2,3-三唑衍生物28 - 33的超声合成、结构表征和生物活性。通过H-和C-NMR光谱以及二维NOESY、HSQC和HMBC方法证实了所制备目标化合物的互变异构结构。对合成的化合物进行了抗增殖测定，结果表明化合物23对慢性髓性白血病细胞（K-562，IC = 2.0 μM）和非霍奇金淋巴瘤细胞（Z-138，IC = 2.0 μM）表现出最高的活性。进一步评估了化合物23对正常外周血单个核细胞（PBMC）的细胞毒性，并研究了其作用机制。评估了合成化合物对革兰氏阳性和革兰氏阴性细菌菌株的抗菌性能。衍生物15 - 17对革兰氏阳性细菌表现出显著的选择性抗菌活性（MIC = 0.25 - 1 μg mL）。此外，在2-芳基苯并咪唑的1,2,3-三唑衍生物中，化合物28和30对表现出较强的选择性活性（MIC = 0.25 μg mL）。
