Natural and Synthetic Chalcones

Cazarolli, Luisa Helena; Kappel, Virgínia Demarchi; Zanatta, Ana Paula; Suzuki, Daniela Ota Hisayasu; Yunes, Rosendo A.; Nunes, Ricardo José; Pizzolatti, Moacir Geraldo; Silva, Fátima Regina Mena Barreto

doi:10.1016/b978-0-444-62615-8.00002-3

Cited by 10 publications

(5 citation statements)

References 153 publications

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“…The chalcone nucleus has been identified as the primary intermediate and is a crucial component of several flavonoids and therapeutic compounds. The primary method for synthesizing chalcone involves the Claisen–Schmidt reaction, which occurs when aromatic aldehydes react with aromatic ketones in the presence of acid or base catalysts . Chalcone serves as a crucial intermediary or starting material for producing different derivatives, including thiazine, pyrazoline, cyanopyridine, oxazoline and isoxazole.…”

Section: Introductionmentioning

confidence: 99%

“…The primary method for synthesizing chalcone involves the Claisen–Schmidt reaction, which occurs when aromatic aldehydes react with aromatic ketones in the presence of acid or base catalysts. 6 Chalcone serves as a crucial intermediary or starting material for producing different derivatives, including thiazine, pyrazoline, cyanopyridine, oxazoline and isoxazole. This is achieved through the cyclization of the α,β-unsaturated carbonyl group in chalcone.…”

Section: Introductionmentioning

confidence: 99%

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Benzyloxychalcone Hybrids as Prospective Acetylcholinesterase Inhibitors against Alzheimer’s Disease: Rational Design, Synthesis, In Silico ADMET Prediction, QSAR, Molecular Docking, DFT, and Molecular Dynamic Simulation Studies

Al-Maqtari,

Hasan,

Suleiman

et al. 2024

ACS Omega

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Acetylcholinesterase inhibitors (AChEIs) are crucial therapeutic targets for both the early and severe stages of Alzheimer's disease (AD). Chalcones and their chromone-based derivatives are well-known building blocks with anti-Alzheimer properties. This study synthesized 4-benzyloxychalcone derivatives and characterized their structures using IR, 1 H NMR, 13 C NMR, and HRMS. Additionally, the synthesized 4-benzyloxychalcone derivatives were tested for anti-acetylcholinesterase (AChE) activity. The synthesized compounds outperformed galantamine, which is used as a positive control against acetylcholinesterase. Utilizing an acetylcholinesterase (AChE) receptor (PDB ID: 4EY7)-chalcone derivative (12a-c), a molecular docking investigation was performed on the synthesized compounds. The goal was to predict the binding sites and energies of the derivatives with respect to the receptor amino acids. The dynamic behavior of the ligand−receptor complex resulting from the interaction of the best docking compounds 12a and 12c with the acetylcholinesterase receptor was used to analyze the stability via MD simulation. MM/GBSA and MM/PBSA were used to calculate free binding energies using snapshots from system trajectories. Advanced computational approaches incorporating long-range corrections were utilized to calculate the molecular characteristics of chalcone derivatives 12a-c at the DFT/wB97XD/6-311++G(d,p) level. We used the molecular electrostatic surface potential (MESP) with high-quality data and visualization to find the most active site in these molecules. Reactivity descriptors, including the condensed Fukui function, chemical hardness (η), dual descriptors, chemical potential (μ), and electrophilicity (ω), were calculated for the chalcone derivatives.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Benzyloxychalcone Hybrids as Prospective Acetylcholinesterase Inhibitors against Alzheimer’s Disease: Rational Design, Synthesis, In Silico ADMET Prediction, QSAR, Molecular Docking, DFT, and Molecular Dynamic Simulation Studies

Al-Maqtari,

Hasan,

Suleiman

et al. 2024

ACS Omega

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“…Chalcones are favored in medicinal chemistry due to their relative ease of production and modification, which reflects the ease with which they are formed in nature [9]. Current chalcone synthetic methodologies are generated through the use of an alkaline base and a polar solvent to link two aromatic molecules, such as acetophenone and benzaldehyde, to generate the core chalcone nucleus [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular docking, bio-evaluation and quantitative structure activity relationship of new chalcone derivatives as antioxidants

Siddiqa

Tajammal

Ahmad

et al. 2023

Journal of Molecular Structure

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“…Natural products can serve as excellent alternatives to insulin due to the perception that they are safe and have fewer side effects. Compound binding to protein targets [8][9][10][11][12] and understanding the molecular mechanics of numerous physiological systems in the cell, such as discovering innovative alternatives to insulin, notably from natural compounds, have dominated the field of computer-aided drug design (CADD) since its debut [13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Identification of Insulin-Mimetic Phytochemicals from Mas Cotek (Ficus deltoidea) for Treatment of Type 2 Diabetes via LC-MS/MS and Molecular Docking Analyses

Man,

Khayat

2023

J Biochem Microbiol Biotechnol

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Type 2 diabetes mellitus, a metabolic syndrome, has become increasingly prevalent in recent years. In the treatment of chronic T2DM, patients are required to take insulin daily, commonly through injections, as the hormone can easily be degraded by the digestive system if taken orally. This can be an uncomfortable experience for the patient. Thus, finding an alternative to insulin, especially from natural compounds, would be beneficial. Ficus deltoidea, which belongs to the Moraceae family, is a medicinal plant known for its anti-diabetic properties. Therefore, this study aimed to identify the phytochemicals from F. deltoidea that mimic insulin by studying their ability to bind to insulin receptors using in silico analysis. A total of 36 phytochemicals were identified in the methanolic extract of F. deltoidea through LC-MS/MS analysis. They were then subjected to molecular docking to determine their binding free energy with the insulin receptor (IR). The results revealed seven phytochemicals with the lowest binding free energy, with 2,3-dihydroxy-N,N'-bis[(E)-1-(4-hydroxy-6-methyl-2-oxochromen-3-yl)ethylideneamino] butanediamide exhibiting the lowest binding free energy at -10.0 kcal/mol. Hence, these phytochemicals demonstrate potential as insulin-mimetic compounds that can be used in the treatment of T2DM.

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Natural and Synthetic Chalcones

Cited by 10 publications

References 153 publications

Benzyloxychalcone Hybrids as Prospective Acetylcholinesterase Inhibitors against Alzheimer’s Disease: Rational Design, Synthesis, In Silico ADMET Prediction, QSAR, Molecular Docking, DFT, and Molecular Dynamic Simulation Studies

Benzyloxychalcone Hybrids as Prospective Acetylcholinesterase Inhibitors against Alzheimer’s Disease: Rational Design, Synthesis, In Silico ADMET Prediction, QSAR, Molecular Docking, DFT, and Molecular Dynamic Simulation Studies

Synthesis, molecular docking, bio-evaluation and quantitative structure activity relationship of new chalcone derivatives as antioxidants

Identification of Insulin-Mimetic Phytochemicals from Mas Cotek (Ficus deltoidea) for Treatment of Type 2 Diabetes via LC-MS/MS and Molecular Docking Analyses

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