Novel N-(Benzyloxy)-6-Fluro-Chromone-2-Carboxamides and N-(Benzyloxy)-Chromone-3-Carboxamides are synthesized from an efficient and straight forward procedure from the reaction of 6-Fluoro-chromone-2-acid and chromone-3-acid with O-(substituted benzyl)-hydroxylamines. The structures of the synthesized compounds are established based on Infrered Radiation (IR), Nuclear Magnetic Resonance (NMR) and MASS spectrometry. Exploration of molecular interaction of the obtained compounds, performed through Discovery Studio v3.5, molecular docking studies with COX-2 enzyme, revealed the high docking scores (Lib Dock) in the range of 113.4-139.0 as compared to celecoxib 145.691. The compounds with high LibDock score were screened for their in vivo analgesic and antiinflammatory activities. Among them, compound 3b displayed good activity and potency.