Synthesis and evaluation of the antibacterial and antifungal activity of new ibuprofen hydrazone derivatives

Abstract

Background and Aims: The pursuit of new antimicrobial agents to address antimicrobial resistance remains a fundamental effort in supporting sustainable global health endeavours. Hydrazone compounds possess numerous advantages as biologically active agents because of their diverse properties. In our work, a series of hydrazone derivatives (4a-f) containing the ibuprofen moiety were synthesised and evaluated as antibacterial and antifungal agents. Methods: Novel hydrazone derivatives were synthesised through the condensation of 2-[4-(2 methylpropyl)phenyl]propanehydrazide with suitable cyclohexanone derivatives. The structure of the new compounds was confirmed using spectral methods such as IR, 1H-NMR, 13C-NMR (APT) and electrospray ionisation mass spectrometry (ESI-MS). Testing involved six compounds and their standards against a range of bacterial and fungal strains, including Gram-positive and Gram-negative bacteria, as well as Candida spp. MIC values were determined using the microbroth dilution method. Results: Each of the tested molecules exhibited varying inhibitory effects across six distinct targets, resulting in different MIC values. Compounds 4a, 4e, and 4f showed moderate antimicrobial activity compared with the standards. Conclusion: Among the tested compounds, compound 4a demonstrated the most potent antimicrobial activity against the P. mirabilis strain, with an MIC value of 312.5 μg/mL. Further modification and development of ibuprofen-hydrazone derivatives against targets may result in new antimicrobial drug candidates in the near future.

Keywords

• Hydrazone
• ibuprofen
• antibacterial activity
• antifungal activity
• gram-positive bacteria
• gram-negative bacteria

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