Synthesis, docking, and biological evaluation of novel 1-benzyl-4-(4-(R)-5-sulfonylidene-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyrrolidin-2-ones as potential nootropic agents

Semenets, Anton; Suleiman, Marharyta M.; Fedosov, A. I.; Shtrygol, S. Yu.; Havrylov, Ihnat O.; Mishchenko, Mariia V.; Kovalenko, Sergiy M.; Georgiyants, Victoriya; Perekhoda, Lina

doi:10.1016/j.ejmech.2022.114823

Cited by 12 publications

(4 citation statements)

References 22 publications

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“…The structural details and data of the target protein were obtained from the Protein Data Bank (PDB‐ID=3R6W) [76] . based on the PASS study the 3R6W protein was selected, the PASS study results are shown in Table 9.…”

Section: Resultsmentioning

confidence: 99%

“…The structural details and data of the target protein were obtained from the Protein Data Bank (PDB-ID = 3R6W). [76] based on the PASS study the 3R6W protein was selected, the PASS study results are shown in Table 9. The process of docking involves the interaction between a flexible protein-ligand complex and a receptor molecule, often a protein, to identify and evaluate favourable interactions between these molecular entities.…”

Section: Molecular Dockingmentioning

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: Molecular Dockingmentioning

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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“…The residue ARG51 exhibits an Amide-Pi Stacked contact with oxygen and nitrogen atoms, whereas ARG51 forms a hydrophobic pi-alkyl connection with the center at distances of 3.80 A°, respectively. The ARG48, CYS86, and VAL88 establish three hydrophobic alkyl interactions with ring centers, denoted at distances of 3.65, 4.19, and 4.68 (Å), respectively [ 94 ]. The computational analysis of molecular docking indicates that the chemical being studied demonstrates a highly favorable binding energy of −7.92 kcal/mol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, solvent role, absorption and emission studies of cytosine derivative

Elangovan,

Arumugam,

Almansour

et al. 2024

Heliyon

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“…To perform calculations in the Autodock 4.2 program, the output formats of the receptor and ligand data were converted to a special PDBQT format. In our previous studies, a similar software package was used [17,18]. The active macromolecule center of the dipeptidyl peptidase-4 (dpp4) (PDB ID: 5Y7J) from the Protein Data Bank (PDB) was used as a biological target for docking.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

The Theoretical Substantiation of the Targeted Search for New DPP4 Inhibitors. Computational Studies of Potential Candidates

Suleiman,

Semenets,

Kobzar

et al. 2024

J. Org. Pharm. Chem.

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Growing evidence suggests that dipeptidyl peptidase 4 (DPP4) inhibitors, in addition to their role in improving glycemic control, help to reduce endothelial dysfunction and have hypolipidemic, anti-atherosclerotic, antitumor, antiviral, and neurotropic properties. This multi-target property may be one of the reasons for repurposing therapeutic treatment strategies with existing agents and the basis for finding new agents to inhibit this target. Based on the structural prerequisites and the evolutionary path of creating DPP4 inhibitors, an inhibitory (R)-β-aminoamide base was used as the basis for constructing potential candidates. It contained a substituted piperazine-2-one derivative and (S)-pyrrolidine-2-carbonitrile fragment, as well as phenyl and diphenyl rings, which were additionally saturated with substituents of various electronic structures, in position 4 of the β-aminoamide chain. The construction of the molecules was carried out taking into account the correspondence of chiral centers to combinations of chiral chains at the DPP4 binding site to possibly prevent a decrease in the inhibitory activity. In silico assessment of the “drug-likeness” and pharmacokinetic profile of the group of compounds studied showed that it had favorable characteristics and could be recommended for further molecular docking in order to predict the likely inhibition of the catalytic activity of DPP4. According to the results of docking, molecules with a moderate and high affinity were found. A detailed analysis of the resulting complexes showed that only nine compounds had a binding mode similar to classical inhibitors. According to the calculated array of values and analysis of the results of docking among the derivatives tested, a hit compound was found as a promising DPP4 inhibitor.

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Synthesis, docking, and biological evaluation of novel 1-benzyl-4-(4-(R)-5-sulfonylidene-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyrrolidin-2-ones as potential nootropic agents

Cited by 12 publications

References 22 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, solvent role, absorption and emission studies of cytosine derivative

The Theoretical Substantiation of the Targeted Search for New DPP4 Inhibitors. Computational Studies of Potential Candidates

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