Novel multi-target directed ligands based on annelated xanthine scaffold with aromatic substituents acting on adenosine receptor and monoamine oxidase B. Synthesis, in vitro and in silico studies.

•Novel tricyclic xanthine derivatives were obtained as potential dual adenosine A2A receptor/monoamine oxidase B ligands.•Potent ligands of adenosine A2A receptors and monoamine oxidase B with nanomolar affinities were found.•Structure–activity relationship for the synthesized series supported by molecular docking for both targets was analyzed.•Selected physicochemical and potential toxic properties were evaluated in in silico and in vitro studies.•Potential antioxidant properties were estimated for selected compounds.