Synthesis, antimicrobial evaluation, crystal structure, Hirschfeld surface analysis and docking studies of 4-[2-(1-methyl-1H-imidazol-2-ylsulfanyl)-acetylamino]-benzenesulfonic acid

Geesi, Mohammed H.; Riadi, Yassine; Kaïba, Abdellah; Ibnouf, Elmutasim O.; Anouar, Elhassane; Dehbi, Oussama; Lazar, S.; Guionneau, Philippe

doi:10.1016/j.molstruc.2022.133425

Cited by 22 publications

(4 citation statements)

References 37 publications

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“…Similarly, the other benzene ring within the GLU188 molecule forms a link within the title compound, with a distance of 3.8 Å. The CH group located in the central backbone forms a hydrogen connection with the CH hydroxyl group in PHE100 PHE151 and MET96, with a distance of 3.6, 4.5, and 3.4, respectively [79] …”

Section: Resultsmentioning

confidence: 99%

“…The CH group located in the central backbone forms a hydrogen connection with the CH hydroxyl group in PHE100 PHE151 and MET96, with a distance of 3.6, 4.5, and 3.4, respectively. [79] The amino group that is connected to the pyrimidine ring exhibits interactions with amino acid residues PRO96, which are located at distances of 5.3. Table 10 presents an overview of the hydrogen bond interactions occurring between the title chemical and amino acids situated at the active site of 3R6W.…”

Section: Conflict Of Interestsmentioning

confidence: 99%

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Synthesis, vibrational analysis, absorption and emission spectral studies, topology and molecular docking studies on sulfadiazine derivative

Elangovan,

Sowrirajan,

Arumugam

et al. 2024

ChemistrySelect

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A new class of (N‐(pyrimidin‐2‐yl)‐4‐((1,7,7‐trimethylbicyclo [2.2.1] heptan‐2‐ylidene) amino) benzenesulfonamide (CDA) was synthesized from commercially available camphor and sulfadiazine. The synthesized Schiff‐base was characterized by FT‐IR, 1H and 13C NMR spectroscopic analyses. The HOMO, LUMO, MEP, chemical reactivity parameters, and NBO were calculated using the WB97XD/cc‐pVDZ basis set. For better understanding, the electronic absorption and emission of the compound were recorded using UV‐Vis and fluorescence spectra. Molecular docking simulations were investigated between ligand (compound) and target protein. The computational results correlate well with observed values. The frontier molecular orbital energy gap (3.78 eV) revealed that the studied molecule has higher polarizability and chemical reactivity with lower kinetic stability. In addition, compound showed the highest binding score −5.72 kcal/mol, which was confirmed by a molecular docking simulation.

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Section: Resultsmentioning

confidence: 99%

Section: Conflict Of Interestsmentioning

confidence: 99%

Synthesis, vibrational analysis, absorption and emission spectral studies, topology and molecular docking studies on sulfadiazine derivative

Elangovan,

Sowrirajan,

Arumugam

et al. 2024

ChemistrySelect

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“…Afterwards a molecular docking study was conducted on the target protein with the assistance of Auto-dock, the docked poses were made visible with the assistance of Discovery Studio Visualizer. [23] 3. RESULTS AND DISCUSSION…”

Section: Synthesis Of (E)-1-(4-chlorophenyl)-n-(nitrophenyl)-methanim...mentioning

confidence: 99%

Synthesis, spectral features, electronic structure studies, and molecular docking analysis of a Schiffbase (E)‐1‐(4‐chlorophenyl)‐N‐(nitrophenyl)methanimine from 4‐chloroaniline and 2‐nitrobenzaldehyde

Diya,

Unni,

Rajimon

et al. 2023

Vietnam Journal of Chemistry

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The compound (E)‐1‐(4‐chlorophenyl)‐N‐(nitrophenyl)methanimine was synthesised and characterised using techniques FTIR, UV‐Vis, NMR and it was compared with the experimental and simulated methods. The compound prepared was optimized using the DFT method employing the basis set B3LYP / cc‐pVDZ. The simulated spectra appeared to be in accordance with the experimental one. The HOMO‐LUMO orbitals and MEP are calculated with the same basis set; the study is chiefly forcasted to the biological activity of the synthesized compound. The wave function regards like localized orbital locator, electron localized function, average localized ionization energy and non‐covalent interaction are also examined as a means of theoretical evidence of the titled compound. The NBO calculations probe the intermolecular and intramolecular movement of charges, and additionally the molecule's stability. The ADMET properties are also considered for the compound with the assistance of Swiss ADMET online tool. The molecular docking analysis was accomplished against the protein (3RW9) of Spermidine dehydrogenase inhibitor employing the software Auto‐dock.

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“… 9 Inhibiting sterol-14-demethylase, the enzyme responsible for a critical step in sterol biosynthesis, has been explored as a potential therapeutic approach against T cruzi and other related parasites. 11 - 13 By targeting this enzyme, it is possible to disrupt the synthesis of essential sterols, which can ultimately lead to the inhibition of parasite growth and survival.…”

Section: Introductionmentioning

confidence: 99%

Machine Learning-Based Approach to Identify Inhibitors of Sterol-14-Alpha Demethylase: A Study on Chagas Disease

Saliu

2024

Bioinform Biol Insights

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Objectives: Chagas Disease, caused by the parasite Trypanosoma cruzi, remains a significant public health concern, particularly in Latin America. The current standard treatment for Chagas Disease, benznidazole, is associated with various side effects, necessitating the search for alternative therapeutic options. In this study, we aimed to identify potential therapeutics for Chagas Disease through a comprehensive computational analysis. Methods: A library of compounds derived from Cananga odorata was screened using a combination of pharmacophore modeling, structure-based screening, and quantitative structure-activity relationship (QSAR) analysis. The pharmacophore model facilitated the efficient screening of the compound library, while the structure-based screening identified hit compounds with promising inhibitory potential against the target enzyme, sterol-14-alpha demethylase. Results: The QSAR model predicted the bioactivity of the hit compounds, revealing one compound to exhibit superior activity compared to benznidazole. Evaluation of the physicochemical, pharmacokinetic, toxicity, and medicinal chemistry properties of the hit compounds indicated their drug-like characteristics, oral bioavailability, ease of synthesis, and reduced toxicity profiles. Conclusion: Overall, our findings present a promising avenue for the discovery of novel therapeutics for Chagas Disease. The identified hit compounds possess favorable drug-like properties and demonstrate potent inhibitory effects against the target enzyme. Further in vitro and in vivo studies are warranted to validate their efficacy and safety profiles.

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Synthesis, antimicrobial evaluation, crystal structure, Hirschfeld surface analysis and docking studies of 4-[2-(1-methyl-1H-imidazol-2-ylsulfanyl)-acetylamino]-benzenesulfonic acid

Cited by 22 publications

References 37 publications

Synthesis, vibrational analysis, absorption and emission spectral studies, topology and molecular docking studies on sulfadiazine derivative

Synthesis, vibrational analysis, absorption and emission spectral studies, topology and molecular docking studies on sulfadiazine derivative

Synthesis, spectral features, electronic structure studies, and molecular docking analysis of a Schiffbase (E)‐1‐(4‐chlorophenyl)‐N‐(nitrophenyl)methanimine from 4‐chloroaniline and 2‐nitrobenzaldehyde

Machine Learning-Based Approach to Identify Inhibitors of Sterol-14-Alpha Demethylase: A Study on Chagas Disease

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