Synthesis, in vitro antifungal evaluation and docking studies of novel derivatives of imidazoles and benzimidazoles

A series of imidazole and benzimidazole derivatives was designed and prepared in good yields via convenient and efficient two steps synthetic route using readily available starting materials. The structures of the synthesized compounds and their intermediates were characterized by IR, H-1-NMR, C-13-NMR spectroscopy, and MS spectra. The in vitro antifungal activities of the targeted compounds were evaluated against Candida Albicans, Cryptococcus neoformans, Aspergillus niger, and Microsporum gypseum. The results showed that some of these azole-derivatives exhibited good to excellent antifungal activities against the used strains especially C. neoformans and A. niger. For example, compound 6b, 1-[2-Phenyl-2-(3-phenyl-propoxy)-ethyl]-1H-imidazole, was quite effective on the C. neoformans, A. niger, and M. gypseum with MIC 1.95 mu g mL(-1). The in silico molecular docking study was also done on the synthesized compounds and the results showed they have minimum binding energy and relatively good affinity toward cytochrome P450. According to the in vitro antifungal results and molecular docking studies, the compounds 6a-d can be selected as lead compounds for further pharmaceutical investigations.