Abstract Synthesis of novel (E)‐N‐(4‐(substituted)benzylidene)‐6‐substituted‐1H‐pyrazolo[3,4‐b]quinoline‐1‐carbothioamides/carboxamides was achieved by the condensation of 6‐substituted‐1H‐pyrazolo[3,4‐b]quinoline‐1‐carbothioamides/carboxamides with substituted benzaldehydes in alcoholic medium in the presence of acetic acid. The structures of synthesized compounds are assigned on the basis of FT IR, 1 H NMR, 13 C NMR and Mass Spectral data. The compounds are subjected for their antibacterial, antifungal and DFT studies. Compounds, (E)‐6‐chloro‐N‐(4‐(dimethylamino)benzylidene)‐1H‐pyrazolo[3,4‐b]quinoline‐1‐carbothioamide (5 b) , (E)‐6‐chloro‐N‐(4‐(dimethylamino)benzylidene)‐1H‐pyrazolo[3,4‐b]quinoline‐1‐carboxamide (5 f) , and (E)‐6‐chloro‐N‐(4‐hydroxybenzylidene)‐1H‐pyrazolo[3,4‐b]quinoline‐1‐carboxamide (5 j) possessed pronounced antibacterial and antifungal activities due to their chemical structure.