Hydroxamic acids with functional group R-CONHOH, have been used as possible inhibitors of metalloenzymes because of their innate ability to strongly bind with metal ions. The synthesis from amides to hydroxamic acids is commonly carried out via a synthetic route wherein hazardous chemicals like acids and extreme reaction conditions are used. Hence, the present study aims to develop a biocatalytic process for the synthesis of a series of hydroxamic acids using the resting cells of Bacillus smithii IIIMB2907. Further, through in silico analysis of the synthesized compounds using molecular docking, molecular dynamics pharmacophore analysis, and density functional theory (DFT) calculations, it was observed that ligand N1-(3-(trifluoromethyl)phenyl)-N8-hydroxyoctanediamide (2c) showed better interaction with class I histone deacetylases (HDACs) on comparisons with FDA approved anti-cancer drug Suberoylanilide hydroxamic acid (SAHA). Furthermore, in vitro HDAC activity of 2c in C2C12 skeletal muscle cell lines validates the potency of this molecule as an HDAC inhibitor, as it shows 33 % HDAC inhibition on comparison with SAHA which showed only 14 % HDAC inhibition. Therefore, this study proposes a novel process for the synthesis of a potential drug candidate that may act as an inhibitor of class I HDAC’s.