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Synthesis and biological activity of novel 2, 5-diamino substituted benzimidazo[1, 2-a]quinolines

Over the past few years substituted benzimidazoles, as a very important and fundamental building skeletons of various essential synthetic and natural pharmacological compounds, have been one of the most extensively studied classes of heterocycles compounds due to their well known biological activities. Because of the structural similarity with naturally occurring compounds such as purine, benzimidazole derivatives can easily interact with biomolecules of the living systems. High fluorescence intensity and possibility of interaction with important biomacromolecules of the living systems offer the potential use of azino fused benzimidazoles as fluorescent probes for detection of important molecules as DNA or different proteins in biomedical diagnostics. As a part of our continuing research in the field of medicinal chemistry, novel 2, 5-diamino substituted benzimidazo[1, 2-a]quinolines were synthesized by uncatalyzed microwave assisted amination. All compounds were characterized by 1H, 13C and NOESY NMR, UV/Vis and fluorimetric spectroscopy and mass spectrometry. Antitumor activity in vitro of prepared compounds was tested on breast, colon and lung carcinoma cell lines. All compounds showed differential activity towards all tested cell lines without the selectivity toward any cell line. To shed more light on the mechanisms of biological action, additional experiments regarded to DNA binding properties of most active compounds were performed.

benzimidazoles ; benzimidazo[1 ; 2-a]quinolines ; antiproliferative activity ; DNA binding ; topoisomerase I

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