Flavonoids are natural phenolic compounds found in dietary sources such as plants, fruits, and vegetables. They have a wide range of biological activities including cytostatic and anti-inflammatory effects. In this research, we synthesized flavone derivatives via the introduction of various aryl functional groups. Furthermore, we combined flavones with gallic acid derivatives. The synthesized compounds were tested against cervical (HeLa) and colon cancer cells (CaCo-2). Moreover, the synthesized compounds were evaluated for their antioxidant and anti-inflammatory activities using DPPH and COX inhibition tests, respectively. The success of the synthesis of our target compounds was confirmed using IR and NMR. Compound 3 potently inhibited the proliferation of CaCo-2 cells (IC50 = 2.42 µg/mL). Meanwhile, compound 4 exhibited antioxidant activity (IC50 = 3.53 ± 0.1 µg/mL). Moreover, compound 4 selectively inhibited COX-2 with an IC50 = 6.02 ± 0.33 µg/mL; it was approximately 6-fold more selective for COX-2 than for COX-1 enzymes. In conclusion, the results strongly indicate that the chemical modification of flavones enhances their bioactivity. Further investigation of in vivo anti-inflammatory and anticancer evaluation of active compounds is required to prove both safety and efficacy.