Synthesis, Antimicrobial Screening, Homology Modeling, and Molecular Docking Studies of a New Series of Schiff Base Derivatives as Prospective Fungal Inhibitor Candidates

Abstract

Twelve new Schiff base derivatives have been prepared by the condensation reaction of different amino substituted compounds (aniline, pyridin-2-amine, o-toluidine, 2-nitrobenzenamine, 4-aminophenol, and 3-aminopropanol) and substituted aldehydes such as nicotinaldehyde, o,m,p-nitrobenzaldehyde, and picolinaldehyde in ethanol using acetic acid as a catalyst. The envisaged structures of the all the synthesized ligands have been confirmed on the basis of their spectral analysis FT-IR, mass spectroscopy, 1H- and 13C-NMR. In vitro screening of their antibacterial and antifungal potential against Escherichia coli bacterium and Fusarium oxysporum f.sp albedinis (F.o.a) fungus, respectively, revealed that all the ligands showed no significant antibacterial activity, whereas most of them displayed good antifungal activity. Homology modeling and docking analysis were performed to explain the antifungal effect of the most and least active compound against two F.o.a fungus proteins.

Gene‐targeted molecular phylogeny, phytochemical analysis, antibacterial and antifungal activities of some medicinal plant species cultivated in Egypt

“…Computational modelling could resolve issues of rare information on the mechanism of action of antifungal molecules that fight pathogens. It could give an atomistic insight into molecular recognition by predicting an antifungal molecule's ability to bind to the active site of the fungal protein 34 . In this study, we docked the tested active molecules of the tested plants with three vital proteins involved in the sclerotial development of the fungus Sclerotinia sclerotiorum .…”

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

“…The modeled proteins structure of Fophy considered as target reported in the literature (Abrigach et al, 2018;Kaddouri et al, 2019;Tighadouini et al, 2019;Toubi et al, 2019) was prepared in Autodock 4 default parameters, and the whole protein was used as grid for blind docking-virtual screening (Table 1) with Perl as launcher of virtual screening for all the ligands in Autodock Vina (Seeliger and de Groot, 2010).…”

“…The selected compounds are all the testes against F.o.a., collected from the references (Waring et al, 2002;Radi et al, 2012Radi et al, , 2015Smaail et al, 2012;Boussalah et al, 2013;Loth et al, 2015;Abrigach et al, 2017Abrigach et al, , 2018Tighadouini et al, 2018Tighadouini et al, , 2019Koudad et al, 2019;Toubi et al, 2019).…”

“…In this study, the rotatable bonds of the ligand flexibility were allowed, while the protein was adopted as a rigid structure. As a first step of this study, the three-dimensional structures of the homology modeled Fophy protein and its template, which is Aspergillus niger phytase (PDB:3K4P) (Gontia-Mishra et al, 2014;Toubi et al, 2019), were aligned using Pymol software (Seeliger and de Groot, 2010), and it is presented in Figure 10.…”

“…A molecular docking approach was used for the best antifungal derivatives against Fophy. The structure of this approach was constructed using the homology model that has been previously reported in the literature (Soundararajan et al, 2011;Abrigach et al, 2014;Tighadouini et al, 2019;Toubi et al, 2019), to achieve better insight into the ligand-receptor binding interactions and direct future synthesis. In case that there is no cofactor, blind docking, and virtual screening are used in this study for site prediction and protocol validation using Autodock Vina (Seeliger and de Groot, 2010) and Dockthor (Santos et al, 2020).…”