Synthesis, molecular docking studies, and biological evaluation of novel alkyl bis(4‐amino‐5‐cyanopyrimidine) derivatives

Boualia, Imen; Derabli, Chamseddine; Boulcina, Raouf; Bensouici, Chawki; Yıldırım, Muhammet; Yıldırım, Arzu Birinci; Mokrani, El Hassen; Debache, Abdelmadjid

doi:10.1002/ardp.201900027

Cited by 12 publications

(3 citation statements)

References 33 publications

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“…It is important to use many assays to prove the effectiveness of each product and their mechanisms like the reductive capacity and radical scavenging, prevention of chain initiation, decomposition of peroxides, prevention of continued hydrogen abstraction . Moreover, inhibition potential against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) key enzymes involved in common human pathologies neurodegenerative disorders was also evaluated.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, antioxidant and anticholinesterase activities of novel quinoline‐aminophosphonate derivatives

Bazine

Cheraiet

Bensegueni

et al. 2020

Journal of Heterocyclic Chem

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A series of 20 novel α-aminophosphonate derivatives bearing quinoline or quinolone moiety was designed and synthesized via Kabachnik-Fields reaction in the presence of triethylammonium acetate as a solvent and catalyst under ultrasound irradiation. This procedure affords products in high yields and short reaction times. Molecular structures of the synthesized compounds 4a-g and 5a-m were confirmed using various spectroscopic methods. The antioxidant activity of these compounds was evaluated by eight complementary in vitro tests. The anticholinesterase activity (AChE, BChE) of these compounds were also evaluated. In addition, theoretical calculations of all compounds were investigated as corrosion inhibitors using density functional theory (DFT). The results revealed that 16 of these compounds exhibited high levels of antioxidant activities depending on the assay and that most compounds showed more potent inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE).H NMR (400 MHz, Chloroform-d 6 ) δ 11.75 (s, 1H, OH), 9.74 (s, 1H, NH), 7.70 (d, J H-P = 3.5 Hz, 1H Ar, H 7 ), 7.10-7.00 (m, 2H Ar, H 1 , H 3, ), 6.93 (dd, J ortho = 8.2, J metha = 1.5 Hz, 1H Ar, H 6 ), 6.88 (dd, J ortho = 7.8, J metha = 1.4 Hz, 1H Ar, H 17 ), 6.72 (td, J ortho = 7.7, J metha = 1.9 Hz, 1H Ar, H 2 ), 6.54 (td, J ortho = 7.6, J metha = 1.4 Hz, 1H Ar, H 18 ), 6.50 (dd, J ortho = 8.4, J metha = 3.6 Hz, 1H Ar, H 16 ), 5.92(d, J = 11.6 Hz, 1H, NH), 5.89(dd, J ortho = 7.8, J metha = 1.7 Hz, 1H, H 15 ), 5.77 (dd, J H-P = 25.0, 11.6 Hz, 1H, H 12 ), 4. 46-4.33 (m, 2H, H 27 ), 4.16-3.91 (m, 2H, H 24 ), 1.20 (t, J = 7.0 Hz, 3H Ar,

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Section: Resultsmentioning

confidence: 99%

Synthesis, antioxidant and anticholinesterase activities of novel quinoline‐aminophosphonate derivatives

Bazine

Cheraiet

Bensegueni

et al. 2020

Journal of Heterocyclic Chem

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“…Missing atoms were added, and formal charges were computed. Then, the resulting structure underwent rigorous minimization before being exported as mol2 files [71]. The 3D structure of each compound was retrieved from the PubChem database (https://pubchem.ncbi.nlm.nih.gov/, accessed on 5 Septembre 2023) and prepared for docking simulations using Maestro, version 11.3, and the LigPrep module (Schrödinger software company, New York, NY, USA) [72].…”

Section: In Silico Molecular Dockingmentioning

confidence: 99%

Exploring the Therapeutic Potential of Ammodaucus leucotrichus Seed Extracts: A Multi-Faceted Analysis of Phytochemical Composition, Anti-Inflammatory Efficacy, Predictive Anti-Arthritic Properties, and Molecular Docking Insights

Djehiche,

Benzidane,

Djeghim

et al. 2024

Pharmaceuticals

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Ammodaucus leucotrichus exhibits promising pharmacological activity, hinting at anti-inflammatory and anti-arthritic effects. This study investigated seed extracts from Ammodaucus leucotrichus using methanol and n-hexane, focusing on anti-inflammatory and anti-arthritic properties. The methanol extract outperformed the n-hexane extract and diclofenac, a reference anti-inflammatory drug, in trypsin inhibition (85% vs. 30% and 64.67% at 125 μg/mL). For trypsin inhibition, the IC50 values were 82.97 μg/mL (methanol), 202.70 μg/mL (n-hexane), and 97.04 μg/mL (diclofenac). Additionally, the n-hexane extract surpassed the methanol extract and diclofenac in BSA (bovine serum albumin) denaturation inhibition (90.4% vs. 22.0% and 51.4% at 62.5 μg/mL). The BSA denaturation IC50 values were 14.30 μg/mL (n-hexane), 5408 μg/mL (methanol), and 42.30 μg/mL (diclofenac). Gas chromatography–mass spectrometry (GC–MS) revealed 59 and 58 secondary metabolites in the methanol and n-hexane extracts, respectively. The higher therapeutic activity of the methanol extract was attributed to hydroxyacetic acid hydrazide, absent in the n-hexane extract. In silico docking studies identified 28 compounds with negative binding energies, indicating potential trypsin inhibition. The 2-hydroxyacetohydrazide displayed superior inhibitory effects compared to diclofenac. Further mechanistic studies are crucial to validate 2-hydroxyacetohydrazide as a potential drug candidate for rheumatoid arthritis treatment.

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“…The co-crystallized ligand of each enzyme was removed and redocked in the active site using GOLD in which the target atoms are fixed, and the ligands are flexible. After successful redocking of the co-crystallized ligand (RMSD value < 1 Å), the same docking parameters were used for M. piperita major compounds [30].…”

Section: Molecular Dockingmentioning

confidence: 99%

Evaluation of In Vitro and In Silico Anti-Alzheimer Potential of Nonpolar Extracts and Essential Oil from Mentha piperita

Srief

Bani

Mokrani

et al. 2023

Foods

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The anticholinesterase and antioxidant activities with chemical composition and molecular docking of essential oil and nonpolar extracts of Mentha piperita were evaluated using enzymatic and chemical methods. Molecular docking tools were used to explain the interaction of the major chemical constituents with the enzymes. GC/MS analyses revealed that the main compounds in M. piperita essential oil were l-menthone (43.601%) followed by pulegone (21.610%), linolenic acid (25.628%), and l-menthone (10.957%), representing the major compounds of the petroleum ether extract. Imidazoquinoline (7.767%) and 17-N-acetyl-oroidine (5.363%) were the major constituents of the chloroform extract. Linolenic acid (19.397%) and l-menthone (6.336%) were the most abundant compounds in the hexane extract. The M. piperita essential oil and nonpolar extracts showed moderate antioxidant activity. The essential oil showed the most promising anticholinesterase activity with IC50 = 10.66 ± 0.12 µg/mL and IC50 = 16.33 ± 0.03 µg/mL against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), respectively, close to galantamine in AChE and more active in BChE, followed by the interesting activity in the petroleum ether extract with IC50 = 23.42 ± 3.06 µg/mL in AChE and IC50 = 62.00 ± 3.22 µg/mL in BChE. The docking experiments showed that among the seven major identified compounds, N-acetyl-17-oroidine showed the highest binding score (63.01 in AChE and 63.68 in BChE). This compound was found to bind the catalytic and peripheral sites, resulting in more potent inhibitory activity than galantamine, which only binds to the catalytic site. These findings suggested the possible use of M. piperita essential oil and nonpolar extracts as a potential source of alternative natural anti-Alzheimer compounds.

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Synthesis, molecular docking studies, and biological evaluation of novel alkyl bis(4‐amino‐5‐cyanopyrimidine) derivatives

Cited by 12 publications

References 33 publications

Synthesis, antioxidant and anticholinesterase activities of novel quinoline‐aminophosphonate derivatives

Synthesis, antioxidant and anticholinesterase activities of novel quinoline‐aminophosphonate derivatives

Exploring the Therapeutic Potential of Ammodaucus leucotrichus Seed Extracts: A Multi-Faceted Analysis of Phytochemical Composition, Anti-Inflammatory Efficacy, Predictive Anti-Arthritic Properties, and Molecular Docking Insights

Evaluation of In Vitro and In Silico Anti-Alzheimer Potential of Nonpolar Extracts and Essential Oil from Mentha piperita

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