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Abstract The present study is concerned with the design, synthesis of new heterocyclic derivatives of ciprofloxacin as a fluoroquinolone member and biological investigation of their antibacterial, antifungal and anticancer activities. Mechanism of antifungal activity of the promising antifungal target compounds is investigated using EDTA based method. This study includes structural elucidation of the new compounds by different spectroscopic and analytical techniques (1H NMR, 13C NMR, LC-MS/MS and elemental microanalysis). Also, the study showed evaluation activity of some compounds against lanosterol 14-alpha demethylase enzyme and molecular docking of some compounds to investigate their binding mode with lanosterol enzyme (PDB: 5esg). The primary results for in vitro antibacterial and antifungal activities showed potent activities of some derivatives compared with the parent compounds. Also, molecular docking study of the promising compounds with higher antifungal activity; they showed good fitting with lanosterol 14-alpha demethylase enzyme (PDB: 5esg) that agreed with obtained in vitro antifungal results. |