Carbohydrate-derived bicyclic selenazolines as new dual inhibitors (cholinesterases/OGA) against Alzheimer’s disease

Velueta-Viveros, Martha; Martı́nez-Bailén, Macarena; Puerta, Adrián; Romero-Hernández, Laura L.; Křen, Vladimı́r; Merino-Montiel, Penélope; Montiel‐Smith, Sara; Fernandes, Miguel X.; Vargas, Ângelo; Padrón, José M.; López, Óscar; Fernandez‐Bolanos, J.

doi:10.1016/j.bioorg.2022.105983

Cited by 6 publications

(2 citation statements)

References 73 publications

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“…28). 213 Because levels of the neurotransmitter acetylcholine and O-GlcNAcase are associated with hyperphosphorylation of tau protein, both O-GlcNAcase and cholinesterase are potentially effective targets for the treatment of Alzheimer's disease. This inhibitor was designed to contain the selenazoline core because it was anticipated that the Se-containing bicyclic structure could better adapt within the key enzyme regions than the isosteric thiazoline structure.…”

Section: Glycosidase Inhibitorsmentioning

confidence: 99%

Glycosidase-targeting small molecules for biological and therapeutic applications

Kim,

Li,

Choi

et al. 2023

Chem. Soc. Rev.

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Section: Glycosidase Inhibitorsmentioning

confidence: 99%

Glycosidase-targeting small molecules for biological and therapeutic applications

Kim,

Li,

Choi

et al. 2023

Chem. Soc. Rev.

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“…Carbohydrate derivatives are an important class of bioactive compounds with a high density of functional groups [ 1 ]. Carbohydrates annulated with heterocycles demonstrate interesting biological properties, including fructose transporter protein GLUT5 inhibition and the selective inhibition of glycoside hydrolase O-GlcNAcase (OGA) or the dual inhibition of OGA and cholinesterases, which are relevant for new therapeutic candidates [ 2 , 3 , 4 ].…”

Section: Introductionmentioning

confidence: 99%

Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones

Kederienė

Rousseau²,

Schuler

et al. 2022

Molecules

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The 1,3-oxazolidine-2-thiones (OZTs) are important chiral molecules, especially in asymmetric synthesis. These compounds serve as important active units in biologically active compounds. Herein, carbohydrate anchored OZTs were explored to develop a copper-catalyzed C-S bond formation with aryl iodides. Chemoselective S-arylation was observed, with copper iodide and dimethylethylenediamine (DMEDA) as the best ligand in dioxane at 60–90 °C. The corresponding chiral oxazolines were obtained in reasonable to good yields under relatively mild reaction conditions. This approach is cheap, as using one of the cheapest transition metals, a simple protocol and various functional group tolerance make it a valuable strategy for getting S-substituted furanose-fused OZT. The structures of the novel carbohydrates were confirmed by NMR spectroscopy and an HRMS analysis.

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Selenium-containing heterocycles

Hou

2023

Privileged Scaffolds in Drug Discovery

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Carbohydrate-derived bicyclic selenazolines as new dual inhibitors (cholinesterases/OGA) against Alzheimer’s disease

Cited by 6 publications

References 73 publications

Glycosidase-targeting small molecules for biological and therapeutic applications

Glycosidase-targeting small molecules for biological and therapeutic applications

Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones

Selenium-containing heterocycles

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