Synthesis, spectral characterizations, computational studies and biological investigation of 4-(4-(2-hydroxyethyl)phenylamino)-4-oxobutanoic acid and its trimethyltin(IV) complex

The current manuscript contains the synthesis, biological evaluation, and theoretical investigations of 4-(4-(2-hydroxyethyl)phenylamino)-4-oxobutanoic acid (HPO) and its organotin(IV) complex (SnHPO). The synthesized compounds were characterized by FT-IR, NMR (1H and 13C), and mass spectrometry. Furthermore, the molecular structures of both compounds were probed by single-crystal X-ray diffraction (SC-XRD)analysis. The outcomes reveal that the chelation occurs by one of the O atoms of the carboxylate group and shows a distorted tetrahedral coordination geometry for the organotin(IV) complex. Both XRD and FT-IR data confirm the monodentate nature of the carboxylate group of HPO. The supramolecular assembly of ligand and complex was stabilized by various intermolecular interactions, which were travelled by Hirshfeld surface analysis (HSA). The experimental and theoretical (based on B3LYP/def2-SVP/6-311G(d,p) level of theory) structures were found to be nearly similar. Mulliken atomic charge and MEP surface indicated Sn, H-N1, and H-O4 atoms in SnHPO are appropriate targets for nucleophilic attacks. The molecular orbital energy gaps suggested that SnHPO possesses high biological activity and chemical reactivity and less stability than HPO. The docking simulation of the synthesized compounds against SARS-CoV-2 virus receptor protein (6LU7) was investigated, and the findings demonstrated that SnHPO has better binding affinity than HPO and favipiravir. The ligand and its complex were vetted for their antifungal and antibacterial activities. It can be concluded that the reported compounds have strong antimicrobial properties but weak hemolytic activity, and they may be studied extensively as potential therapeutic drugs for a variety of microbes.