Coumarin based Schiff base proligands as promising antioxidant, antibacterial and anticancer agents: DFT and molecular docking correlations

In drug development, coumarin scaffolds are widely used to treat various illnesses, including cancer. Here, we report the biological potentials of Schiff base compounds derived from 3-acetyl coumarin with N4-cyclohexyl thiosemicarbazide (3a), carbohydrazide (3b), 1, 3 diamino-2-propanol (3c) and 1, 3 diaminoguanidine hydrochloride (3d). The chemical structures were elucidated by a range of spectroscopic methods including MALDI MS and NMR. Single crystal X-ray diffraction study confirms the structure of thiosemicarbazone (3a). For each of the ligands 3a-3d, theoretical supports were provided using density functional theory calculations. ADME analysis enables to anticipate the compounds as probable medication. The in vitro evaluation of the compounds for antioxidant activity using 2, 2-diphenyl-1-picrylhydrazyl displays significant results with impressive IC50 values in the range 7.6-12.94 mu M compared with IC50 value 14.85 mu M of the standard ascorbic acid. Antibacterial activity of these substances was also examined in vitro against a gram-positive (Staphylococcus aureus) and a gram-negative (Escherichia coli) bacteria. The MTT test was used to examine the anticancer activity against human papillary cancer cell line (MDA T32). MDA T32 is found to be effectively inhibited by these proligands. Additionally, molecular docking experiments have been used with PDB IDs 1BNA, 3RP8 (antioxidant), 3FY8 and 2ANQ (antibacterial) to correlate the experimental study. The results reveal that the diaminoguanidine dihydrazone 3d could be a promising lead compound.