Antibacterial and Urease Inhibitory activity of New Piperazinyl N-4 Functionalized Ciprofloxacin-oxadiazoles

Abstract

This research includes design of new ciprofloxacin bearing oxadiazole at the N-4 piperazinyl for the purpose of having urease inhibitory activity as well as antibacterial activity. Hence, a group of new N-4 piperazinyl oxdiazole derivatives of ciprofloxacin was prepared and characterized using different spectroscopic and analytical techniques including 1 H-NMR, 13 C-NMR, MS and elemental analysis. Compounds 5b and 5c experienced moderate activity against the urease producing Klebsiella pneumoniae strains better than the standard drug used chloramphenicol and less than the parent drug ciprofloxacin. On the other hand, most of the tested compounds showed a urease inhibitory activity more than the parent drug, ciprofloxacin and comparable to standard, thiourea. The docked compounds exhibited better binding to urease enzyme of H. pylori than standard, AHA with binding scores for correlate to the antiurease assay results. Compound 5b was the most potent anti-Klebsiella pneumoniae urease inhibitor with activity higher the standard (IC 50 = 67.8 and 78.89 µM, respectively).

Design and synthesis of new N-thioacylated ciprofloxacin derivatives as urease inhibitors with potential antibacterial activity

“…Along the same line, the urease inhibitory and antibacterial activities of the ciprofloxacin-piperazinyl derivatives were proved (Fig. 1 , compound C ) 30 . These results demonstrated the critical role of ciprofloxacin as a critical building block for the design of anti-urease agents.…”

Vanillin-Based Indolin-2-one Derivative Bearing a Pyridyl Moiety as a Promising Anti-Breast Cancer Agent via Anti-Estrogenic Activity

“…The solubility of compound 6j in various solvents (methanol, ethanol, and acetonitrile) was evaluated by adding an excess amount of the drug in a stoppered container with 0.5 mL aliquots of the used solvent. Continuous shaking was carried out in a water bath at 37 ± 1 °C for 48 h. Aliquots of the filtrate were adequately diluted with a suitable solvent and analyzed using HPLC as previously reported. , The in silico ADME study of compound 6j was performed via the SwissADME server (), and some physicochemical properties, lipophilicity, water solubility, pharmacokinetics, and drug-likeness properties were calculated. ,, …”

“…Continuous shaking was carried out in a water bath at 37 ± 1 °C for 48 h. Aliquots of the filtrate were adequately diluted with a suitable solvent and analyzed using HPLC as previously reported. 68 , 69 The in silico ADME study of compound 6j was performed via the SwissADME server ( ), and some physicochemical properties, lipophilicity, water solubility, pharmacokinetics, and drug-likeness properties were calculated. 44 , 70 , 71 …”

Synthesis and molecular docking of new N4-piperazinyl ciprofloxacin hybrids as antimicrobial DNA gyrase inhibitors

“…All plates were incubated at 37 ºC for 24 h. The inhibition zones were measured, and their average was calculated. The MIC was calculated by plotting the natural logarithm of the concentration of each dilution of the tested compounds against the square of zones of inhibition, and a regression line was drawn through the points then the antilogarithm of the intercept on the logarithm of concentration axis gave the MIC value [57].…”

“…The samples were immersed in a water bath thermostatized at 37 ± 1 • C and 100 rpm and periodically shaken for 48 h. Once the equilibrium was reached, the pH of the supernatant was regarded. Aliquots of the filtrate properly diluted with suitable buffer were analyzed by UV spectrophotometry (Shimadzu UV A-160) at the maximum wavelengths (λ max 272 nm) [57,59].…”