This is the first report, to our knowledge, of molecular docking studies on 2-amino-3-cyano-4H-chromenes 4a–o and 6a–h with the active site of CYP51 of Candida spp., and topoisomerase I. Due to the encouraging results, in which some chromene compounds displayed better binding energy, inhibition and cytotoxicity than the reference compounds, the two series of derivatives are good candidates for future research on the design and development of new 2-amino-3-cyano-4H-chromenes, with dual activity against cancer and fungal infections. The gene discussed is CYP51A1; the disease is cancer.