Chalcones (1,3-diaryl-2-propen-1-ones) are one of the best known naturally occurring biological active compounds belonging to flavonoid family. They possess wide range of biological properties such as; anti-cancer, anti-bacterial, antiinflammatory, anti-angiogenic. In addition, chalcone boronic acid derivatives have been tested for their anti-cancer properties and saccharide sensors abilities in few of the recent studies. In those studies, it is speculated that boronic acid chalcone derivatives are selectively cytotoxic against cancer cells rather than healthy cells. In the present study, synthesis of simple chalcones, derivatized by two boronic acids, and 2-naphthyl chalcones having a single boronic acid are reported first time in literature. For this purpose different commercially available acetylphenyl boronic acid and formylphenyl boronic acid derivatives are reacted in alkaline methanol to yield diboronic acid chalcone compounds. Similarly condensation reaction of 2-naphthaldehyde with different acetylphenyl boronic acids yielded the monoboronic acids derivatized 2-naphthyl chalcones. Synthesized diboronic acid chalcone derivatives and 2-naphthyl calcone boronic acid derivatives were tested for their anti-cancer properties against human mammary adenocarcinoma cancer cell lines (MCF-7), and human prostate cancer cell lines (PC3). Their aromatase inhibition potentials were also reported first time in here. In addition, their binding capabilities upon D-fructose, Dgalactose and D-glucose of these compounds in physiologic pH were also examined.