•Novel thiosemicarbazones synthesized from carbonyl compounds and thiosemicarbazide.•Compounds characterized using UV-Vis and FT-IR spectral techniques.•Demonstrated potent antibacterial activity against Bacillus subtilis and Escherichia coli.•Exhibited significant antidiabetic activity, surpassing acarbose in molecular docking.•Promising candidates WS-1 and WS-2 showed lowest binding energies with Alpha-glucosidase. Thiosemicarbazones and their derivatives were synthesized by reacting carbonyl compounds with thiosemicarbazide, followed by treatment with metal salts. The prepared thisemicarbazones such as (2E)-2-(1,5,7-trichloronaphthalen-2-yl)-methylidene-hydrazine-1-carbothioamide,(2E)-2-(1,5,7-trihydroxynaphthalen-2-yl)-methylidenehydrazine-1-carbothioamide and these were characterized by using diverse spectral techniques, such as UV–Vis and FT-IR. The synthesized compounds were subsequently evaluated for their antibacterial properties against Gram(+) Bacillus subtilis and Gram(-) Escherichia coli, using ciprofloxacin as a reference, as well as for their anti-microbial activities. For the evaluation of anti-diabetic activity, Acarbose served as the reference. Molecular docking results indicated that WS-1 and WS-2 exhibited superior performance against Alpha-glucosidase proteins, evidenced by their lowest binding energies (−8.1 and −8.3 kcal/mol) respectively compared to other ligands. These findings suggest that WS-1 and WS-2 are promising candidates for further research and development by pharmaceutical companies to explore additional biological activities. Display omitted