Synthesis of novel DNA-intercalating naphthopyrone derivatives with improved water solubility and photophysical properties

The efficient synthesis of several novel DNA-intercalating furonaphthopyrone derivatives with improved water solubility or photophysical properties are described. As expected, all new compounds can efficiently intercalate into DNA with higher or comparable binding affinity relative to the parent naphthopyranone. The highest binding affinity is found for the aminomethyl derivative and may result from its good water solubility and the electrostatic interaction between the amino group and the DNA phosphate backbone. The described synthetic methodology could be utilized in the preparations of other analogs with different skeletons.