Synthesis, in vitro antifungal evaluation and in silico study of 3-azolyl-4-chromanone phenylhydrazones
Journal Title: DARU Journal of Pharmaceutical Sciences - Year 2012, Vol 20, Issue 0
Abstract
The currently available antifungal drugs suffer from toxicity, greatest potential drug interactions with other drugs, insufficient pharmacokinetics properties, and development of resistance. Thus, development of new antifungal agents with optimum pharmacokinetics and less toxicity is urgent task. In the search for new azole antifungals, we have been previously described azolylchromanone oxime ethers as rigid analogs of oxiconazole. In continuation of our work, we incorporated phenylhydrazone moiety instead of oxime ether fragment in azolylchromanone derivatives.Methods The 3-azolyl-4-chromanone phenylhydrazones were synthesized via ring closure of 2-azolyl- 2'-hydroxyacetophenones and subsequent reaction with phenylhydrazine. The biological activity of title compounds was evaluated against different pathogenic fungi including Candida albicans, Saccharomyces cerevisiae, Aspergillus niger, and Microsporum gypseum. Docking study, in silico toxicity risks and drug-likeness predictions were used to better define of title compounds as antifungal agents.Results The in vitro antifungal activity of compounds based on MIC values revealed that all compounds showed good antifungal activity against C. albicans, S. cerevisiae and M. gypseum at concentrations less than 16 mug/mL. Among the test compounds, 2-methyl-3- imidazolyl derivative 3b showed the highest values of drug-likeness and drug-score. Conclusion The 3-azolyl-4-chromanone phenylhydrazones considered as analogs of 3-azolyl-4- chromanone oxime ethers basically designed as antifungal agents. The antifungal activity of title compounds was comparable to that of standard drug fluconazole. The drug-likeness data of synthesized compounds make them promising leads for future development of antifungal agents.
Authors and Affiliations
Adile Ayati, Hamid Irannejad, Saeed Emami, Mehraban Falahati
Keywords
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