A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2Hbenzo[f]indazole-4,9-dione (10) and fused compounds as 2-hydroxy-3-(4- hydroxy-7-methoxy-2-oxo-1,2 dihydroquinolin-3-yl)naphthalene-1,4-dione (7) and naphtha [2,3-b]furan-3,4,9(2H)-trione (6) based on Lawsone ‘that plays as important precursor’ was synthesized by reaction with 1,3- diphenyl-1H-pyrazole-4-carbaldehyde and halo-compounds, such as 2- chloro-acetyl chloride or 3-bromo-4-hydroxy-7-methoxyquinolin-2(1H)-one. Spectra and elemental analysis of newly synthesized compounds were investigated. The target molecules were showed easy access to antioxidant (calorimetrical measurement) and antitumor (Ehrlich ascites carcinoma [EAC] cells) activities. Geometrical isomers (enol, Keto conformers, and syn, anti-conformers) were achieved by density functional theory (DFT) that conformed to the spectral analysis of the investigated compounds.