Spectral Analysis and Biological Evaluation of 3,5-Dimethyl-1-[2-(1-methyltetrazol-5-yl)-sulfanylacetyl]-2,6-diphenyl-piperidin-4-one: Crystal Structure, Hirshfeld Surface, Antimicrobial Activity and Dipeptidyl Peptidase IV Inhibition

A single crystal of 3,5-dimethyl-1-[2-(1-methyltetrazol-5-yl)sulfanylacetyl]-2,6-diphenyl-piperidin-4-one (DMTSDPO) has been synthesized and extensively characterized using analytical techniques, which involves 1H NMR, infrared, mass spectroscopy and single crystal X-ray diffraction (SXRD). DMTSDPO is a triclinic crystal system with P-1 space group, with cell dimensions a = 13.301(3) Å; b = 17.687(4) Å; c = 20.615(4) Å and α = 89.928(10)º; β = 89.760(11)º; γ = 72.648(10)º, V = 4628.7(16) and Z = 8. The molecular structure was identified through conservative method and refined with SHELXL-97, which produced a final R-value of 0.0446. The Hirshfeld surface evaluation has been employed to determine the power of interactions involving hydrogen bonds between molecular pairs, revealing predominant contributions from H···H and N···H intermolecular contacts. The derivatives were subjected to in vitro antimicrobial assays against bacterial and fungal strains, with DMTSDPO exhibiting significant activity against E. coli. The elusive mechanism of action for piperidine derivatives prompted a molecular docking study, shedding light on the active site region, binding modes and interactions of active site residues with dipeptidyl peptidase IV (DPP4). This investigation contributes to a detailed understanding of the compounds mechanism of action and holds promise for the design of novel, potent drug molecules.