6-[(4-Fluorophenyl)(1H-imidazol-1-yl)methyl]-1,3-benzodioxol-5-ol and 6-[(4-methoxyphenyl)(1H-imidazol-1-yl)methyl]-1,3-benzodioxol-5-ol

The title compounds, C17H13FN2O3 and C18H16N2O4, are new potent aromatase inhibitors combining the common features of second‐ and third‐generation nonsteroid anti‐aromatase compounds. The molecules have a propeller shape, with dihedral angles between adjacent planes in the range 49–86°. A quantum mechanical ab initio Roothaan–Hartree–Fock calculation for the isolated molecules shows values for these angles close to the ideal value of 90°. Docking studies of the molecules in the aromatase substrate show that their strong inhibitor potency can be attributed to molecular flexibility, hydrophobic interactions, heme Fe coordination and hydrogen bonding.