Design, synthesis and evaluation of hydrazine and acyl hydrazone derivatives of 5-pyrrolidin-2-one as antifungal agents - Université de technologie de Compiègne Access content directly
Journal Articles Bioorganic and Medicinal Chemistry Letters Year : 2020

Design, synthesis and evaluation of hydrazine and acyl hydrazone derivatives of 5-pyrrolidin-2-one as antifungal agents

Abstract

Twenty-eight 5-pyrrolidine-2-ones decorated by hydrazine or acyl hydrazones groups have been designed, synthesized and evaluated as antifungal agents on a panel of twelve fungal strains and three non albicans candida yeasts species which have demonstrated reduced susceptibility to commonly used antifungal drugs. Half of the target compounds exhibited good to high antifungal activities on at least one strain with MIC50 lower than the control antifungal agent – hymexazol or ketoconazole. 5-Arylhydrazino-pyrrolidin-2-ones were found active and the –NH-NH- linker proved to be essential to maintain the antifungal potential. Compound 2a is a broad-spectrum antifungal, active on 60% of the tested strains. Replacing the hydrazine linker by an acylhydrazone one narrowed the spectrum of activity but pyroglutamylaryl hydrazones, mainly aromatic ones, exhibited good activity, adequate “fungicide-like” properties and were devoted of cytotoxicity.
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Dates and versions

hal-02902219 , version 1 (20-05-2022)

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Attribution - NonCommercial

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Anca-Elena Dascalu, Alina Ghinet, Emmanuelle Lipka, Christophe Furman, Benoît Rigo, et al.. Design, synthesis and evaluation of hydrazine and acyl hydrazone derivatives of 5-pyrrolidin-2-one as antifungal agents. Bioorganic and Medicinal Chemistry Letters, 2020, 30 (13), pp.127220. ⟨10.1016/j.bmcl.2020.127220⟩. ⟨hal-02902219⟩
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