(2016) Phthalimide-Derived N-Benzylpyridinium Halides Targeting Cholinesterases: Synthesis and Bioactivity of New Potential Anti-Alzheimer's Disease Agents. Archiv der Pharmazie. pp. 293-301.
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Abstract
In order to develop potent dual-binding cholinesterase inhibitors as potential drugs for the treatment of Alzheimer's disease, we designed and synthesized phthalimide-based acetylcholinesterase (AChE) inhibitors (7) containing a substituted N-benzylpyridinium residue. The in vitro anti-cholinesterase assay employing the target compounds against AChE and butyrylcholinesterase (BChE) revealed the 2-fluorobenzylpyridinium derivative 7d as the most potent compound against both enzymes, with IC50 values of 0.77 and 8.71 μM. The docking study of compound 7d into the active site of AChE showed the gorge-spanning binding mode, in which the compound spans the narrow hydrophobic gorge from the bottom to the rim. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
| Item Type: | Article |
|---|---|
| Keywords: | 1 (2 bromobenzyl) 4 (1,3 dioxoisoindolin 2 yl)methylpyridin 1 ium chloride; 1 (2,4 dichlorobenzyl) 4 (1,3 dioxoisoindolin 2 yl)methylpyridin 1 ium chloride; 1 (2,6 dichlorobenzyl) 4 (1,3 dioxoisoindolin 2 yl)methylpyridin 1 ium chloride; 1 (3 bromobenzyl) 4 (1,3 dioxoisoindolin 2 yl)methylpyridin 1 ium chloride; 1 (3 bromobenzyl) 4 (2,5 dioxopyrrolidin 1 yl)methylpyridin 1 ium bromide; 1 (3,4 dichlorobenzyl) 4 (1,3 dioxoisoindolin 2 yl)methylpyridin 1 ium chloride; 1 (4 bromobenzyl) 4 (1,3 dioxoisoindolin 2 yl)methylpyridin 1 ium chloride; 1 benzyl 4 (1,3 dioxoisoindolin 2 yl)methylpyridin 1 ium bromide; 1 benzyl 4 (2,5 dioxopyrrolidin 1 yl)methylpyridin 1 ium bromide; 4 (1,3 dioxoisoindolin 2 yl)methyl 1 (2 nitrobenzyl)pyridin 1 ium bromide; 4 (1,3 dioxoisoindolin 2 yl)methyl 1 (4 nitrobenzyl)pyridin 1 ium bromide; 4 (1,3 dioxoisoindolin 2 yl)methyl1 (2 fluorobenzyl)pyridin 1 ium chloride; 4 (1,3 dioxoisoindolin 2 yl)methyl1 (2,3,5 trifluorobenzyl)pyridin 1 ium chloride; 4 (1,3 dioxoisoindolin 2 yl)methyl1 (3 fluorobenzyl)pyridin 1 ium chloride; 4 (1,3 dioxoisoindolin 2 yl)methyl1 (4 fluorobenzyl)pyridin 1 ium chloride; 4 (2,5 dioxopyrrolidin 1 yl)methyl 1 (3 fluorobenzyl)pyridin 1 ium bromide; acetylcholinesterase; cholinesterase; cholinesterase inhibitor; halide; phthalimide derivative; pyridinium derivative; succinimide derivative; unclassified drug, Article; cholinesterase inhibition; drug activity; drug design; drug potency; drug synthesis; enzyme active site; enzyme binding; IC50; in vitro study; kinetics; molecular docking; priority journal; structure activity relation |
| Page Range: | pp. 293-301 |
| Journal or Publication Title: | Archiv der Pharmazie |
| Volume: | 349 |
| Number: | 4 |
| Publisher: | Wiley-VCH Verlag |
| Depositing User: | ms soheila Bazm |
| URI: | http://eprints.ssu.ac.ir/id/eprint/9935 |
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