New pyrrole derivatives as DNA gyrase and 14α‐demethylase inhibitors: Design, synthesis, antimicrobial evaluation, and molecular docking

Hilmy, Khaled M. H.; Kishk, Fawzya N. M.; Shahen, Esmat B. A.; Sobh, Eman A.; Hawata, Mohamed A.

doi:10.1002/ddr.22080

Cited by 3 publications

(1 citation statement)

References 49 publications

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“…This concept has motivated researchers to discover many antifungals that inhibit 14-αdemethylase activity. 48,49 The target compounds (ligand and its complexes) showed experimentally antifungal activities against C. albicans, and the Co (II) complex showed boosted activity that confirms the role of the complexation on the enhancement of the activity of the ligand concerning the reference ketoconazole. The binding interaction of the ligand and its Co (II) complex on CYP51 may support that hypothesis.…”

Section: Docking As Antifungal Agentsmentioning

confidence: 70%

Spectral, XRD, morphological, DFT, and molecular modeling investigations of newly prepared isatin Schiff base complexes

Moustafa,

Omar,

Qayed

et al. 2024

Applied Organom Chemis

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The new Schiff base ligand was designed from a condensation reaction of isatin with 5‐amino‐2‐hydroxy benzoic acid. Then, the metal complexes were prepared. The structures of the prepared compounds were framed from thermogravimetric analyses (TG–DTG), mass spectrometry, elemental analyses, 1H‐NMR, IR, electronic spectra, UV–vis, and conductivity measurements. Surface and size morphology have been studied by X‐ray powder diffraction and scanning electron microscope (SEM) analysis. The IR spectra suggested that the ligand acted as bidentate coordinated with metal ions through deprotonated carboxylate oxygen atom and oxygen of phenolic group. With the exception of the complexes of Cr (III), Fe (III), and Cd (II), which were non‐electrolytes, the molar conductivities demonstrated the electrolytic behavior of all the rest complexes. The X‐ray diffraction (XRD) analysis patterns for the Schiff base complexes indicated their crystalline nature except the Co (II) complex which had amorphous structure. The ligand and its metal complexes were screened for their antimicrobial activities against two G‐positive, two G‐negative bacteria and against Aspergillus fumigatus and Candida albicans fungi. Additionally, the compounds were evaluated against the MFC‐7 breast cancer cell line for their anticancer activity. The outcomes demonstrated their strong antitumor activity. [Fe(HL)Cl2(H2O)2]0.5H2O complex has the lowest IC50 value = 9 μg mL−1. Molecular modeling studies for the ligand and its Co (II) and Fe (III) complexes were accomplished from density functional theory (DFT) analysis. From molecular docking study, the electrophilic moieties in both complexes displayed good binding interactions with the CDK6, aminoglycoside phosphotransferase, and CYP51 targeted proteins.

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Section: Docking As Antifungal Agentsmentioning

confidence: 70%

Spectral, XRD, morphological, DFT, and molecular modeling investigations of newly prepared isatin Schiff base complexes

Moustafa,

Omar,

Qayed

et al. 2024

Applied Organom Chemis

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In Silico Design and In Vitro Assessment of Bicyclic Trifluoromethylated Pyrroles as New Antibacterial and Antifungal Agents

Hodyna,

Klipkov,

Kachaeva

et al. 2024

Chemistry & Biodiversity

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QSAR studies on the number of compounds tested as S. aureus inhibitors were performed using an interactive Online Chemical Database and Modeling Environment (OCHEM) web platform. The predictive ability of the developed consensus QSAR model was q2 = 0.79 ± 0.02. The consensus prediction for the external evaluation set afforded high predictive power (q2 = 0.82 ± 0.03). The models were applied to screen a virtual chemical library with anti‐S. aureus activity. Six promising new bicyclic trifluoromethylated pyrroles were identified, synthesized and evaluated in vitro against S. aureus, E. coli, and A. baumannii for their antibacterial activity and against C. albicans, C. krusei and C. glabrata for their antifungal activity. The synthesized compounds were characterized by 1H, 19F, and 13C NMR and elemental analysis. The antimicrobial activity assessment indicated that trifluoromethylated pyrroles 9 and 11 demonstrated the greatest antibacterial and antifungal effects against all the tested pathogens, especially against multidrug‐resistant strains. The acute toxicity of the compounds to Daphnia magna ranged from 1.21 to 33.39 mg/L (moderately and slightly toxic). Based on the docking results, it can be suggested that the antibacterial and antifungal effects of the compounds can be explained by the inhibition of bacterial wall component synthesis.

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Unlocking the Potential of Pyrrole: Recent Advances in New Pyrrole-Containing Compounds with Antibacterial Potential

Rusu,

Oancea,

Tanase

et al. 2024

IJMS

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Nitrogen heterocycles are valuable structural elements in the molecules of antibacterial drugs approved and used to treat bacterial infections. Pyrrole is a five-atom heterocycle found in many natural compounds with biological activity, including antibacterial activity. Numerous compounds are being develop based on the pyrrole heterocycle as new potential antibacterial drugs. Due to the phenomenon of antibacterial resistance, there is a continuous need to create new effective antibacterials. In the scientific literature, we have identified the most relevant studies that aim to develop new compounds, such as pyrrole derivatives, that are proven to have antibacterial activity. Nature is an endless reservoir of inspiration for designing new compounds based on the structure of pyrrole heterocycles such as calcimycin, lynamycins, marinopyrroles, nargenicines, phallusialides, and others. However, many other synthetic compounds based on the pyrrole heterocycle have been developed and can be optimized in the future. The identified compounds were classified according to the type of chemical structure. The chemical structure–activity relationships, mechanisms of action, and antibacterial effectiveness of the most valuable compounds were highlighted. This review highlights scientific progress in designing new pyrrole-containing compounds and provides examples of lead compounds that can be successfully optimized further.

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New pyrrole derivatives as DNA gyrase and 14α‐demethylase inhibitors: Design, synthesis, antimicrobial evaluation, and molecular docking

Cited by 3 publications

References 49 publications

Spectral, XRD, morphological, DFT, and molecular modeling investigations of newly prepared isatin Schiff base complexes

Spectral, XRD, morphological, DFT, and molecular modeling investigations of newly prepared isatin Schiff base complexes

In Silico Design and In Vitro Assessment of Bicyclic Trifluoromethylated Pyrroles as New Antibacterial and Antifungal Agents

Unlocking the Potential of Pyrrole: Recent Advances in New Pyrrole-Containing Compounds with Antibacterial Potential

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