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Synthesis and antiproliferative activity of nitro and amino substituted benzimidazoles and benzothiazoles

Nowadays heterocyclic compounds become unavoidable structural motifs and building blocks in organic and medicinal chemistry. Since benzimidazoles and benzothiazoles as one of the most important nitrogen heterocycles have great and versatile biological activities, these benzazoles become important structural scaffolds in the rational design of novel drugs in medicinal and pharmaceutical chemistry. These nitrogen scaffolds could be found in a variety of bioactive natural and synthetic medical and biochemical agents, which possess different chemical and pharmacological features. Within this work we present the synthesis, structural characterization and biological evaluation of methoxy and hydroxy substituted 2-benzimidazole and 2-benzothiazole derivatives bearing either nitro or protonated amino group at the benzazole scaffold (Figure 1). The targeted compounds were prepared by using conventional and well-optimized reactions of organic chemistry for the synthesis and cyclocondensation of benzimidazole and benzothiazole nuclei. All synthesized compounds were structurally characterized by means of 1H and 13C NMR spectroscopy. The antiproliferative activity was evaluated on the panel of human cancer cells in vitro. Some of tested compounds showed prominent antiproliferative activity. Obtained results revealed the strong influence of the substituents placed at the phenyl as well as on the benzazole nuclei on biological activity.

antiproliferative activity, benzimidazoles, benzothiazoles, synthesis

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