The synthesis of some new linear furobenzopyrone 3a-h, 7a,b and angular furobenzopyrone derivatives 9a-s and 12a,b were described on the base of being monofunctional compounds to decrease possible toxicity. All the prepared compounds were evaluated for their antimicrobial and photosensitizing activities. Compounds 2e, 4 and 7b were found to have good antimicrobial activity while only compound 2e exhibited higher photosensitizing activity than xanthotoxin. In addition, photosensitizing activity increased upon increasing time of radiation and concentration of substance. Quantitative structure–activity relationship (QSAR) study was applied to find a correlation between the photosensitizing activities of the newly synthesized furobenzopyrone derivatives and their physicochemical parameter. Furthermore, docking study was undertaken to gain insight into the possible binding mode of these compounds with the binding site of the DNA gyrase (topoisomerase II) enzyme which is responsible for resolving topological problems which arise during the various processes of DNA.