Design, synthesis and biological evaluation of 2-styryl-5-hydroxy-4-pyrone derivatives and analogues as multiple functional agents with the potential for the treatment of Alzheimer’s disease

Hu, Chenxian; Liu, Jiang; Tang, Li; Zhang, Minkui; Sheng, Rong

doi:10.1016/j.bmc.2021.116306

Cited by 11 publications

(3 citation statements)

References 29 publications

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“…As a scaffold, γ-pyranone and the natural antioxidants it contains can scavenge ROS and reduce oxidative damage to reverse the pathological progress of AD. 23,24 For instance, Cheng et al 25 and Hu et al 26 designed and synthesized various γ-pyranone-based functional agents with antioxidant effects and the ability to chelate metal ions and inhibit Aβ aggregation, demonstrating their potential for AD treatment.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of the kojic acid dimer and its potential for the treatment of Alzheimer's disease

Liu

et al. 2023

RSC Med. Chem.

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Section: Introductionmentioning

confidence: 99%

Synthesis and properties of the kojic acid dimer and its potential for the treatment of Alzheimer's disease

Liu

et al. 2023

RSC Med. Chem.

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“…Hence, developing cholinesterase inhibitors with antioxidant capabilities may benefit the neurotransmitter action in AD patients [ 24 , 25 ]. Besides the inhibitory activity, the antioxidative activity has an additional positive pleiotropic effect in increasing both the level and duration of neurotransmitter activity.…”

Section: Introductionmentioning

confidence: 99%

Resveratrol–Maltol and Resveratrol–Thiophene Hybrids as Cholinesterase Inhibitors and Antioxidants: Synthesis, Biometal Chelating Capability and Crystal Structure

et al. 2022

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New resveratrol–thiophene and resveratrol–maltol hybrids were synthesized as cholinesterase inhibitors and antioxidants. As with photostability experiments, biological tests also found remarkable differences in the properties and behavior of thiophene and maltol hybrids. While resveratrol–thiophene hybrids have excellent inhibitory and antioxidant properties (similar to the activity of reference drug galantamine), maltols have been proven to be weaker inhibitors and antioxidants. The molecular docking of selected active ligands gave insight into the structures of docked enzymes. It enabled the identification of interactions between the ligand and the active site of both cholinesterases. The maltols that proved to be active cholinesterase inhibitors were able to coordinate Fe3+ ion, forming complexes of 1:1 composition. Their formation constants, determined by spectrophotometry, are very similar, lgK = 11.6–12.6, suggesting that Fe3+ binds to the common hydroxy-pyranone moiety and is hardly affected by the other aromatic part of the ligand. Accordingly, the characteristic bands in their individual absorption spectra are uniformly red-shifted relative to those of the free ligands. The crystal structures of two new resveratrol–maltol hybrids were recorded, giving additional information on the molecules’ intermolecular hydrogen bonds and packing. In this way, several functionalities of these new resveratrol hybrids were examined as a necessary approach to finding more effective drugs for complicated neurodegenerative diseases.

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“…2H-pyran-2-one moiety, a cyclic lactone shows its significant presence in natural products and are essential building blocks in synthetic organic and medicinal chemistry [13][14][15][16][17][18]. Owing to their profound biological activities, we focused our research interest on pyranones and their transformation into potential biologically active scaffolds [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Microwave‐assisted decarboxylation of 2H‐Pyran‐3‐carboxylic acid derivatives under basic condition

Mishra

Bal

2022

Journal of Heterocyclic Chem

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Despite the availability of several methods for decarboxylation, this area remains exploratory and requires new development. Here, we report a highly efficient microwave‐assisted hydrodecarboxylation of 4‐(methylthio)‐2‐oxo‐6‐aryl‐2H‐pyran‐3‐carboxylic acids (1a‐k) under basic condition to obtain 4‐(methylthio)‐6‐aryl‐2H‐pyran‐2‐ones (2a‐k) with >90% yield. The requirement of proton source from the solvent was observed by performing the reactions of 1b and 1e in CD3OD to obtain deuterated compounds 2 l and 2 m respectively. All compounds were characterized by spectroscopic analysis. Further, compounds 2b and 2e were analyzed by single‐crystal X‐ray diffraction studies.

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Design, synthesis and biological evaluation of 2-styryl-5-hydroxy-4-pyrone derivatives and analogues as multiple functional agents with the potential for the treatment of Alzheimer’s disease

Cited by 11 publications

References 29 publications

Synthesis and properties of the kojic acid dimer and its potential for the treatment of Alzheimer's disease

Synthesis and properties of the kojic acid dimer and its potential for the treatment of Alzheimer's disease

Resveratrol–Maltol and Resveratrol–Thiophene Hybrids as Cholinesterase Inhibitors and Antioxidants: Synthesis, Biometal Chelating Capability and Crystal Structure

Microwave‐assisted decarboxylation of 2H‐Pyran‐3‐carboxylic acid derivatives under basic condition

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