Synthesis, biological screening, POM, and 3D-QSAR analyses of some novel pyrazolic compounds

Abrigach, Farid; Karzazi, Y.; Benabbes, Redouane; Youbi, M. El; Khoutoul, Mohamed; Taïbi, Nadia; Karzazi, N.; Benchat, N.; Bouakka, Mohammed; Saalaoui, Ennouamane; Touzani, Rachid

doi:10.1007/s00044-017-1888-8

Cited by 17 publications

(12 citation statements)

References 32 publications

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“…These findings can be possibly interpreted by the absence of pharmacophore sites which can act as potential and specific features to inhibit the growth of bacteria. 47,48 In contrast, most of these molecules exhibit potent antifungal activity against FOA in a manner dependent on the dose as indicated in Table 3. Their activity strongly depends on the structure activity relationships (SARs) and shows an interesting influence of the substitution pattern.…”

Section: Journal Of Chemical Information and Modelingmentioning

confidence: 99%

Novel β-keto–enol Pyrazolic Compounds as Potent Antifungal Agents. Design, Synthesis, Crystal Structure, DFT, Homology Modeling, and Docking Studies

Tighadouini

Radi

Abrigach

et al. 2019

J. Chem. Inf. Model.

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A new family of promising inhibitors bearing -keto-enol functionality with greatly improved pharmacophore properties has prepared. Herein, a series of novel derivatives of -keto-enol group embedded with pyrazolic moiety has been designed and synthesized via a one-step procedure using mixed Claisen condensation in the attempt to develop potential antifungal agents. The structures of the synthesized compounds were confirmed by elemental analysis, FT-IR, ESI/LC-MS, 1 H and 13 C NMR. In addition, X-ray diffraction analysis (XRD) was used to determine the single crystal structure of compound 10. All the newly compounds have been evaluated for their in vitro antifungal and antibacterial activities. Interestingly, the results indicate that most of the compounds display notable antifungal activity close to that of the benomyl fungicide taken as the standard drug. For the most active compound and for benomyl, a correlation has been evidenced between the experimental antifungal activity and the theoretical predictions by DFT calculations and molecular docking against Fgb1 protein.

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Section: Journal Of Chemical Information and Modelingmentioning

confidence: 99%

Novel β-keto–enol Pyrazolic Compounds as Potent Antifungal Agents. Design, Synthesis, Crystal Structure, DFT, Homology Modeling, and Docking Studies

Tighadouini

Radi

Abrigach

et al. 2019

J. Chem. Inf. Model.

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“…The fact that the ligands had a double carbon-nitrogen link may have contributed to the increased activity of the complexes. It was discovered that the metal ions in the complexes possessed a positive charge, implying that it is somewhat complementary to the donor atoms in ligands and that π-electron delocalization may occur throughout the chelate . The metal complexes gained a lipophilic feature as a result of the chelation, which helps their absorption through the lipid membrane of microbes .…”

Section: Resultsmentioning

confidence: 99%

Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations

Noreen

Sumrra

2021

ACS Omega

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During the current study, the new aminothiazole Schiff base ligands (S 1 ) and (S 2 ) were designed by reacting 1,3thiazol-2-amine and 6-ethoxy-1,3-benzothiazole-2-amine separately with 3-methoxy-2-hydroxybenzaldehyde in good yields (68−73%). The ligands were characterized through various analytical, physical, and spectroscopic (FT-IR, UV−Vis, 1 H and 13 C NMR, and MS) methods. The ligands were exploited in lieu of chelation with bivalent metal (cobalt, nickel, copper, and zinc) chlorides in a 1:2 (M:L) ratio. The spectral (UV−Vis, FT-IR, and MS), as well as magnetic, results suggested their octahedral geometry. The theoretically optimized geometrical structures were examined using the M06/6-311G+(d,p) function of density function theory. Their bioactive nature was designated by global reactivity parameters containing a high hardness (η) value of 1.34 eV and a lower softness (σ) value of 0.37 eV. Different microbial species were verified for their potency (in vitro), revealing a strong action. The Gram-positive Micrococcus luteus and Gram-negative Escherichia coli gave the highest activities of 20 and 21 mm for compounds (8) and ( 7), respectively. The antifungal activity against the Aspergillus niger and Aspergillus terreus species gave the highest activities of 20 and 18 mm for compounds ( 7) and ( 6), respectively. The antioxidant activity, evaluated as DPPH and ferric reducing power, gave the highest inhibition (%) as 72.0 ± 0.11% (IC 50 = 144 ± 0.11 μL) and 66.3% (IC 50 = 132 ± 0.11 μL) for compounds (3) and (8), respectively. All metal complexes were found to be more biocompatible than free ligands due to their chelation phenomenon. The energies of LUMOs had a link with their activities. ■ HIGHLIGHTS• A facile synthesis of aminothiazole-containing Schiff bases and their metal chelates. • Combined experimental and theoretical exploration to decide their medicinal role. • Geometry optimization studies at the M06/6-311G +(d,p) level of density function theory. • The relative order of medicinal studies was as follows:reference drugs > metal chelates > ligands.

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“…Unfortunately, the results of the preliminary screening showed that none of the tested compounds were found to exhibit antibacterial effect against the used bacterium. These results can be explained by the high resistance of the E.coli strain to this kind of product, or also by the absence of active or pharmacophore sites which can act as specific and potential features to inhibit the growth of this bacterium [19].…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2019

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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.

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Synthesis, biological screening, POM, and 3D-QSAR analyses of some novel pyrazolic compounds

Cited by 17 publications

References 32 publications

Novel β-keto–enol Pyrazolic Compounds as Potent Antifungal Agents. Design, Synthesis, Crystal Structure, DFT, Homology Modeling, and Docking Studies

Novel β-keto–enol Pyrazolic Compounds as Potent Antifungal Agents. Design, Synthesis, Crystal Structure, DFT, Homology Modeling, and Docking Studies

Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations

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

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