engleski

Relationships between NMR spectroscopic features, molecular descriptors and druglikeness parameters of some fluoroquinolone salts

The NMR spectroscopic features of trovafloxacin (TVA) mesylate, pefloxacin (PFX) mesylate dihydrate and ciprofloxacin (CIP) hydrochloride monohydrate were studied in DMSO-d6 solution with the aim of investigating the effects of substituents and the type of salt on the NMR parameters of fluoroquinolone and fluoronaphthyridine ring systems. For this purpose, the 1H and 13C NMR methods were used. Relationships between 1H and 13C NMR chemical shifts (ppm) of fluoronaphthyridone and fluoroquinolone ring systems, calculated molecular descriptors (MDs) and drug-likeness scores (DLSs), computed for cationic species of investigated fluoroquinolone salts were explored. The topological polar surface area (TPSA), the lipophilicity (miLogP), the relative molecular mass (Mr) and the volume (V), and computed molecular descriptors (MDs), the G protein-coupled receptor ligand-likeness (GPCR ligand-ls), the ion channel ligandlikeness (ICL-ls), the kinase inhibitor-likeness (KI-ls) and the nuclear receptor ligand-likeness (NRL-ls) scores were used in this study. The 1H NMR chemical shifts (ppm) of protons in COOH, H5 and (NHn)+, as well as 13C NMR chemical shifts (ppm) of C4, C5 and C11 shown to be good parameters in exploration of property-property and property-drug-likeness relationships for investigated fluoroquinolone salts.

QSAR; fluoroquinolone antibiotics; fluoroquinolone salts; molecular descriptors; NMR chemical shifts; drug-likeness

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