Computational and experimental characterisation of a new (R)-camphor-Thiazolidinone derivative: A combined approach for structure optimisation and activity prediction

This study describes the synthesis, characterisation, in-silico exploration, and theoretical investigation of a novel 5-Methyl-2-(((1S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)hydrazono)thiazolidin-4-one 3. The structure of the synthesised derivative was successfully confirmed using high-resolution mass spectrometry (HRMS) and ¹H and ¹³C nuclear magnetic resonance (NMR) spectroscopy. In addition, a concise theoretical study was employed to elucidate the experimentally observed stability of the compound. On the computational level, this investigation utilised DFT, molecular docking, and molecular dynamics simulations for the (R)-camphor-thiazolidinone derivative. The optimised structure of compound 3 was predicted with the DFT/B3LYP method with the 6–311++G(d,p) basis set. The theoretical vibrational modes were assigned and found to be consistent with the observed FT-IR spectrum. The simulated NMR values exhibited good agreement with the experimental NMR chemical shifts, with the deviations of 0.5113 and 3.816 ppm for the 1H and 13C, respectively. The UV–vis spectra indicated the n → π* and π → π* transitions in compound 3, with confirmation of intermolecular charge transfer (ICT) from the FMOs and NBO analyses. The MEP surface, Mulliken, and NPA analyses confirm the presence of reactive sites within compound 3. NCI-RDG studies revealed the presence of van der Waals (vdW) interactions and the absence of hydrogen bonding within the studied molecule. The molecular docking analysis indicates that compound 3 exhibits a strong inhibitory effect on the targeted protein 6HQO, which, in turn, is associated with breast cancer. The molecular dynamics analysis validates the accuracy of the docking results.