Cancer is a complex disease and one of the major health problems worldwide. Thus, the discovery of new drugs that can be used for this purpose becomes urgent. Nature is an important source of new drugs, so the demand for natural products, or their derivatives, with therapeutic action, has grown over time. Among the natural products of pharmacological interest are flavonoids, a class of bioactive compounds found in plant kingdom. Some flavonoid classes comprise chiral molecules with one or more stereogenic centers, having some of the times different biological activity. Our team has already extensive experience in the synthesis of chiral flavonoid derivatives and previous results showed that some of these compounds had a high inhibitory effect on tumor cell growth. Thus, the aim of this project is to further explore some of the most promising compounds already selected, namely concerning the role of the stereochemistry in their activity, the mechanisms inducing cell death, anti-mitotic activity or metabolic effects, their capacity to inhibit mechanisms of resistance in cancer cells and to analyze the potential of combining them with other chemotherapeutic drugs in cancer treatment.