Biochemical and pharmacological evaluation of 4-hydroxychromen-2-ones bearing polar C-3 substituents as anticoagulants

► Fifteen synthesized coumarin compounds were examined as in vivo anticoagulants. ► Four compounds, 2b, 4c, 5c and 9c, presented in vivo activity. ► Coumarin molecular target, VKORC1, was homology-modeled. ► Results were discussed using 3D-QSAR, molecular docking and DFT mechanistic studies. ► Coumarin metabolic pathways were obtained.