engleski

Synthesis and antitumor evaluations of novel 2-aryl substituted benzimidazole derivatives

Benzimidazole is an important pharmacophore and represents a privileged structure in medicinal chemistry.[1] Its derivatives show numerous pharmacological activities such as antituberculostatic, antimalarial, antimicrobial, antiviral, antitumor and anti- inflammatory.[2] The 1, 2, 3-triazole products are more than passive linkers, they readily associate with biological targets, through hydrogen-bonding and dipole interactions and attract a lot of attention as pharmacophores.[3] In this paper, we present ultrasonic and microwave cyclization reaction of O-alkylated benzaldehydes with variously substituted 1, 2-diaminobenzene which gave 2- arylbenzimidazole derivatives. 1, 2, 3-triazolyl benzimidazole derivatives were prepared by Huisgen 1, 3-dipolar cycloaddition reaction using copper(II) acetate as catalyst. Antitumoral evaluations of all tested compounds revealed that the 2-arylbenzimidazole derivative with N, N- diethyl substituent showed the most pronounced activity against antitumor cell lines: pancreatic adenocarcinoma (Capan-1, IC50=2.2 μM), lung carcinoma (NCI-H460, IC50=2.2 μM), acute lymphoblastic leukemia (DND-41, IC50=2.6 μM), chronic myeloid leukemia (K- 562, IC50=2.0 μM) and non-Hodgkin lymphoma (Z-138, IC50=2.0 μM).

benzimidazole ; 1, 2, 3- triazole ; click kemija

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