Two new enaminone ligands, 3-chloro-4-{(4-chlorophenyl)amino}pent-3-en-2-one (Ac-PCA), 4-(benzylamino)-3-chloropent-3-en-2-one (Ac-BA) and their metal complexes with transition metal ions [Cu(II), Cd(II) and Co(II)] were prepared and subsequently characterized by FTIR, ICP-AES, UV-Vis, TGA, 1H NMR, 13C NMR and FAB-MS. These newly synthesized compounds were further investigated for anti-acetylcholinesterase (AChE) and anti-urease activities. The (Ac-BA)Cu(II) complex exhibited good anti-AChE while (Ac-BA)2Co(II) complex was potent against anti-urease activities. Other ligands and complexes showed poor to no enzyme inhibitory activities. The synthesized compounds were docked inside acetylcholinesterase enzymes to determine their putative binding mode.