Interest of novel N-alkylpyridinium-indolizine hybrids in the field of Alzheimer's disease: Synthesis, characterization and evaluation of antioxidant activity, cholinesterase inhibition, and amyloid fibrillation interference

Baussanne, Isabelle; Firstova, Olga; Dediu, Andreea Botezatu; Larosa, Camille; Furdui, Bianca; Ghinea, Ioana Ottilia; Thomas, Aline; Chierici, Sabine; Dinică, Rodica Mihaela; Demeunynck, Martine

doi:10.1016/j.bioorg.2021.105390

Cited by 14 publications

(3 citation statements)

References 70 publications

(67 reference statements)

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“…The introduction of the second chlorine into the 2-or 3-position (120r (IC 50 = 78 nM) and 120n (IC 50 > 300 nM)] of 2-chlorobenzyl derivative 120b showed a reduction in the anti-AChE activity, while the introduction of fluorine into Particularly, the comparison of the compound 120a with the compound 120p (IC 50 = 147 nM) or 120q (IC 50 = 100 nM) indicated that the switching of sulfur with oxygen or NH did not have suitable effect on the anti-AChE activity. Baussanne et al (2021) reported the synthesis of N-alkylpyridinium-indolizine hybrids and evaluated them against ChEs (Supplementary Scheme S24).…”

Section: Figurementioning

confidence: 99%

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Recent developments in the design and synthesis of benzylpyridinium salts: Mimicking donepezil hydrochloride in the treatment of Alzheimer’s disease

et al. 2022

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Background: Alzheimer’s disease (AD) is an advanced and irreversible degenerative disease of the brain, recognized as the key reason for dementia among elderly people. The disease is related to the reduced level of acetylcholine (ACh) in the brain that interferes with memory, learning, emotional, and behavior responses. Deficits in cholinergic neurotransmission are responsible for the creation and progression of numerous neurochemical and neurological illnesses such as AD.Aim: Herein, focusing on the fact that benzylpyridinium salts mimic the structure of donepezil hydrochlorideas a FDA-approved drug in the treatment of AD, their synthetic approaches and inhibitory activity against cholinesterases (ChEs) were discussed. Also, molecular docking results and structure–activity relationship (SAR) as the most significant concept in drug design and development were considered to introduce potential lead compounds. Key scientific concepts: AChE plays a chief role in the end of nerve impulse transmission at the cholinergic synapses. In this respect, the inhibition of AChE has been recognized as a key factor in the treatment of AD, Parkinson’s disease, senile dementia, myasthenia gravis, and ataxia. A few drugs such as donepezil hydrochloride are prescribed for the improvement of cognitive dysfunction and memory loss caused by AD. Donepezil hydrochloride is a piperidine-containing compound, identified as a well-known member of the second generation of AChE inhibitors. It was established to treat AD when it was assumed that the disease is associated with a central cholinergic loss in the early 1980s. In this review, synthesis and anti-ChE activity of a library of benzylpyridinium salts were reported and discussed based on SAR studies looking for the most potent substituents and moieties, which are responsible for inducing the desired activity even more potent than donepezil. It was found that linking heterocyclic moieties to the benzylpyridinium salts leads to the potent ChE inhibitors. In this respect, this review focused on the recent reports on benzylpyridinium salts and addressed the structural features and SARs to get an in-depth understanding of the potential of this biologically improved scaffold in the drug discovery of AD.

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Section: Figurementioning

confidence: 99%

“… Baussanne et al (2021) reported the synthesis of N -alkylpyridinium-indolizine hybrids and evaluated them against ChEs ( Supplementary Scheme S24 ).…”

Section: Introductionmentioning

confidence: 99%

Recent developments in the design and synthesis of benzylpyridinium salts: Mimicking donepezil hydrochloride in the treatment of Alzheimer’s disease

et al. 2022

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“…Indolizines are privileged molecular scaffolds in synthetic heterocyclic chemistry and in drug discovery [1], being present in relevant biologically active compounds [2][3][4], and with a variety of applications in materials science owing to their prominent photophysical properties [5,6]. This type of heterocycle exhibits varied activities based on the substituted indolizines shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Catalyst‐free oxidative [3+2]‐annulation of (2‐nitroethene‐1,1‐diyl)bis(methylsulfane) and pyridinium ylides: Efficient synthesis of (methylsulfanyl)indolizines heterocycles

Chen

Liu

Yang

et al. 2023

Journal of Heterocyclic Chem

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The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

Antón-Cánovas

Alonso

2022

Angewandte Chemie

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C-H bond formylation is the most immediate way to incorporate the versatile formyl group into (hetero)aromatics. However, the type of reagents and severe conditions involved in the classical formylation methods often curtail their application, especially in the presence of other functional groups. Herein, we present the Eschenmoser's salt, a commercially available (dimethylamino)methylating chemical, as a useful reagent for the C-H formylation of indolizines and other compounds. The method is straightforward and mild, furnishing indolizinecarbaldehydes in modest-to-good yields with exclusive and remote regioselectivity. Furthermore, these compounds can be easily transformed into pushpull dyes and are highly selective in the colorimetric detection of nitrite, a substance extensively employed as preservative in the food industry, the concentration of which is crucial to control to prevent harmful effects in living organisms. The assay is simple, allowing the naked-eye detection of nitrite in solution or on a cotton swab for a wide range of concentrations.

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Interest of novel N-alkylpyridinium-indolizine hybrids in the field of Alzheimer's disease: Synthesis, characterization and evaluation of antioxidant activity, cholinesterase inhibition, and amyloid fibrillation interference

Cited by 14 publications

References 70 publications

Recent developments in the design and synthesis of benzylpyridinium salts: Mimicking donepezil hydrochloride in the treatment of Alzheimer’s disease

Recent developments in the design and synthesis of benzylpyridinium salts: Mimicking donepezil hydrochloride in the treatment of Alzheimer’s disease

Catalyst‐free oxidative [3+2]‐annulation of (2‐nitroethene‐1,1‐diyl)bis(methylsulfane) and pyridinium ylides: Efficient synthesis of (methylsulfanyl)indolizines heterocycles

The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

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