Tel-Cu-NPs Catalyst: Synthesis of Naphtho[2,3-g]phthalazine Derivatives as Potential Inhibiters of Tyrosinase Enzymes and Their Investigation in Kinetic, Molecular Docking, and Cytotoxicity Studies

Selvaraj, Keerthana; Ali, Daoud; Alarifi, Saud; Idhayadhulla, Akbar

doi:10.3390/catal10121442

Cited by 10 publications

(7 citation statements)

References 30 publications

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“…The grid parameters and active sites were obtained from literature. [44] Further details about docking methodology are from. [45,46] The ADMET characteristics are determined using pkCSM (online software) and Smiles were generated to analyze examined compounds.…”

Section: Computational Methodology Detailsmentioning

confidence: 99%

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Synthesis and Computational Exploration of Morpholine Bearing Halogenated Sulfonamides as Potential Tyrosinase Inhibitors

Abbasi

Raza

Siddiqui

et al. 2023

Chemistry & Biodiversity

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In the presented work, a novel series of three different 4‐((3,5‐dichloro‐2‐[(2/4‐halobenzyl)oxy]phenyl)sulfonyl)morpholines was synthesized and the structure of these compounds were corroborated by 1H‐NMR & 13C‐NMR studies. The in vitro results established all the three compounds as potent tyrosinase inhibitors relative to the standard. The Kinetics mechanism plots established that compound 8 inhibited the enzyme non‐competitively. The inhibition constants Ki calculated from Dixon plots for this compound was 0.0025µM. Additionally, computational techniques were used to explore electronic structures of synthesized compounds. Fully optimized geometries were further docked with tyrosinase enzyme for inhibition studies. Reasonably good binding/interaction energies and intermolecular interactions were obtained. Finally, drug likeness was also predicted using the rule of five (RO5) and Chemical absorption, distribution, metabolism, excretion, and toxicity (ADMET) characteristics. It is anticipated that current experimental and computational investigations will evoke the scientific interest of the research community for the above‐entitled compounds.

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Section: Computational Methodology Detailsmentioning

confidence: 99%

“…MGL tools [43] were used for the preparation of proteins i. e., water molecules and inhibitors were removed for getting free protein and polar hydrogens were added to the receptors. The grid parameters and active sites were obtained from literature [44] . Further details about docking methodology are from [45,46] .…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Computational Exploration of Morpholine Bearing Halogenated Sulfonamides as Potential Tyrosinase Inhibitors

Abbasi

Raza

Siddiqui

et al. 2023

Chemistry & Biodiversity

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“…However, the grid dimensions were also confirmed by locating the residues interacting with co-crystallized inhibitors. 59 After docking, the 3-D and 2-D interactions of FTEAA with amino acid residues were visualized by the Biovia Discovery Studio visualizer (2020).…”

Section: Computational Methodologymentioning

confidence: 99%

“…A configuration file was prepared, and the grid centers and grid dimensions were set according to the prereported literature. However, the grid dimensions were also confirmed by locating the residues interacting with co-crystallized inhibitors . After docking, the 3-D and 2-D interactions of FTEAA with amino acid residues were visualized by the Biovia Discovery Studio visualizer (2020).…”

Section: Computational Methodologymentioning

confidence: 99%

Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

et al. 2022

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Ethyl 4-(4-fluorophenylamino)-2,6-bis(4-(trifluoromethyl)phenyl)-1-(4-fluoro-phenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate ( FTEAA ) has been synthesized efficiently in an iodine-catalyzed five-component reaction of 4-fluoroaniline, 4-trifluoromethyl benzaldehyde, and ethyl acetoacetate in methanol at 55 °C for 12 h. Various spectro-analytical techniques such as 1 H and 13 C NMR and Fourier-transform infrared spectroscopy have validated the structure of FTEAA . Further confirmation of the structure of FTEAA has been established on the basis of single-crystal X-ray diffraction analysis. The supramolecular assembly of FTEAA in terms of strong and comparatively weak noncovalent interactions is fully investigated by Hirshfeld surface analysis, the interaction energy between pairs of molecules, and energy frameworks. The void analysis is conducted to explore the strength and stability of the crystal structure. Furthermore, molecular docking analysis was computationally performed to see the potential intermolecular interactions between the selected proteins and FTEAA . The binding interaction energies are found to be −8.8 and −9.6 kcal/mol for the proteins MAO-B (PDB ID: 2V5Z ) and MAO-A (PDB ID: 2Z5X ), respectively. These reasonably good binding energies (more negative values) indicate the efficient associations between the FTEAA and target proteins. The proteins and FTEAA were also analyzed for intermolecular interactions. FTEAA and proteins interact in a variety of ways, like conventional hydrogen bonds, carbon–hydrogen bonds, alkyl, π-alkyl, and halide interactions.

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“…This reaction was catalyzed by ultrasmall Pd NPs generated in situ [381]. Telmisartan-stabilized Cu NPs were utilized to synthesize naphtho[2,3-g]phthalazine derivatives as potential inhibitors of tyrosinase enzymes [382]. NPs in an oxidant/catalyst system.…”

Section: Othersmentioning

confidence: 99%

Recent Progress of Metal Nanoparticle Catalysts for C–C Bond Forming Reactions

Ohtaka¹

2021

Catalysts

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Over the past few decades, the use of transition metal nanoparticles (NPs) in catalysis has attracted much attention and their use in C–C bond forming reactions constitutes one of their most important applications. A huge variety of metal NPs, which have showed high catalytic activity for C–C bond forming reactions, have been developed up to now. Many kinds of stabilizers, such as inorganic materials, magnetically recoverable materials, porous materials, organic–inorganic composites, carbon materials, polymers, and surfactants have been utilized to develop metal NPs catalysts. This review classified and outlined the categories of metal NPs by the type of support.

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Tel-Cu-NPs Catalyst: Synthesis of Naphtho[2,3-g]phthalazine Derivatives as Potential Inhibiters of Tyrosinase Enzymes and Their Investigation in Kinetic, Molecular Docking, and Cytotoxicity Studies

Cited by 10 publications

References 30 publications

Synthesis and Computational Exploration of Morpholine Bearing Halogenated Sulfonamides as Potential Tyrosinase Inhibitors

Synthesis and Computational Exploration of Morpholine Bearing Halogenated Sulfonamides as Potential Tyrosinase Inhibitors

Exploring Highly Functionalized Tetrahydropyridine as a Dual Inhibitor of Monoamine Oxidase A and B: Synthesis, Structural Analysis, Single Crystal XRD, Supramolecular Assembly Exploration by Hirshfeld Surface Analysis, and Computational Studies

Recent Progress of Metal Nanoparticle Catalysts for C–C Bond Forming Reactions

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