Synthesis, Biochemical Characterization, and Theoretical Studies of Novel β-Keto-enol Pyridine and Furan Derivatives as Potent Antifungal Agents

Abstract

In the present study, we report the design and synthesis of new derivatives of the β-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), 1 H NMR, 13 C 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 IC 50 = 12.83 μg/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.

Construction of 1,2,4-triazole-fused heterocycles via an amine oxidase-inspired catalyst

“…27 These heteroarenes are also employed as ligands in organometallic/coordination chemistry, vide infra . 13 a , m ,28 Furthermore, the bicyclic/polycyclic aromatic amines, such as biphenyl methylamine 2u , 2-naphthylmethylamine 2v , and 9-anthracenemethanamine 2w , can also be used as the coupling partners, delivering the products in 69–81% yields.…”

Novel family of bis-pyrazole coordination complexes as potent antibacterial and antifungal agents

“…These results were compared to several reported ligand and complexes with potential antibacterial behaviors and proved to be better to competitive. 51–53…”

Mono-Alkylated Ligands Based on Pyrazole and Triazole Derivatives Tested Against Fusarium oxysporum f. sp. albedinis: Synthesis, Characterization, DFT, and Phytase Binding Site Identification Using Blind Docking/Virtual Screening for Potent Fophy Inhibitors

“…where After that, several tests were done to find the volume of the ligand to 50% of inhibition experimentally not doing the linear regression, with the objective to calculate the concentration of ligand needed to inhibit 50% of the F.o.a. (Radi et al, 2015;Tighadouni et al, 2016;Koudad et al, 2019;Tighadouini et al, 2020).…”