Journal
ACS OMEGA
Volume 5, Issue 28, Pages 17743-17752Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.0c02365
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Funding
- bilateral WBI action with Morocco (COP 22 Program 2018-2022)
- Fonds De La Recherche Scientifique.FNRS [CDR 33694457]
- PPRP10 CNRST project (Morocco)
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In the present study, we report the design and synthesis of new derivatives of the beta-keto-enol grafted on pyridine and furan moieties (L-1-L-11). Structures of compounds were fully confirmed by Fourier transform infrared spectroscopy (FT-IR), H-1 NMR, C-13 NMR, electrospray ionization/liquid chromatography-mass spectrometry (ESI/LC-MS), and elemental analysis. The compounds were screened for antifungal and antibacterial activities (Escherichia coli, Bacillus subtilis, and Micrococcus luteus). In vitro evaluation showed significant fungicidal activity for L-1, L-4, and L-5 against fungal strains (Fusarium oxysporum f.sp albedinis) compared to the reference standard. Especially, the exceptional activity has been demonstrated for L-1 with IC50 = 12.83 mu g/mL. This compound and the reference benomyl molecule also showed a correlation between experimental antifungal activity and theoretical predictions by Petra/Osiris/Molinspiration (POM) calculations and molecular coupling against the Fgb1 protein. The highest inhibition of bacterial growth for L-1 is due to its strongest binding to the target protein. This report may stimulate the further synthesis of examples of this substance class for the development of new drugs.
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