Synthesis, X-ray diffraction study, analysis of inter-molecular inter-actions and mol-ecular docking of ethyl 1-(3-tosyl-quinolin-4-yl)piperidine-4-carboxyl-ate.

ABSTRACT: The title compound, C₂₄H₂₆N₂O₄S, can be obtained via two synthetic routes. According to our investigations, the most suitable way is by the reaction of ethyl 2-bromo-acetate with sodium tosyl-sulfinate in dry DMF. It was crystallized from methanol into the monoclinic P2₁/n space group with a single mol-ecule in the asymmetric unit. Hirshfeld surface analysis was performed to define the hydrogen bonds and analysis of the two-dimensional fingerprint plots was used to distinguish the different types of inter-actions. Two very weak non-classical C-H⋯O hydrogen bonds were found and the contributions of short contacts to the Hirshfeld surface were determined. Mol-ecules form an isotropic network of inter-molecular inter-actions according to an analysis of the pairwise inter-action energies. A mol-ecular docking study evaluated the inter-actions in the title compound with the active centers of macromolecules of bacterial targets (Staphylococcus aureus DNA Gyrase PDB ID: 2XCR, Mycobacterium tuberculosis topoisomerase II PDB ID: 5BTL, Streptococcus pneumoniae topoisomerase IV PDB ID: 4KPF) and revealed high affinity towards them that exceeded the reference anti-biotics of the fluoro-quinolone group.

SUBMITTER: Vaksler Y 

PROVIDER: S-EPMC9443802 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature