Abstract
A series of novel hybrid spiro heterocycles comprising pyrrolizine, spiroxindole and piperidine moieties was synthesized chemo-, regio- and stereoselectively in good yields from 1,3-dipolar cycloaddition reaction of a series of 1-acryloyl-3,5-bisarylmethylidenepiperidin-4-ones with azomethine ylides generated in situ from 5-choloroisatin and l-proline in methanol. These cycloadducts displayed significant cholinesterase inhibitory activity. Among the compounds screened, 8g and 8e, showed maximum inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinestrase (BChE) with IC50 values of 3.33 and 3.13μM, respectively.
Copyright © 2013 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Butyrylcholinesterase / metabolism
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Cholinesterase Inhibitors / chemical synthesis
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Cholinesterase Inhibitors / chemistry
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Cholinesterase Inhibitors / pharmacology*
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Cholinesterases / metabolism*
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Cyclization
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Dose-Response Relationship, Drug
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Indoles / chemical synthesis
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Indoles / chemistry
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Indoles / pharmacology*
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Models, Molecular
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Molecular Structure
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Oxindoles
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Piperidines / chemical synthesis
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Piperidines / chemistry
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Piperidines / pharmacology*
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Pyrroles / chemical synthesis
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Pyrroles / chemistry
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Pyrroles / pharmacology*
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Spiro Compounds / chemical synthesis
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Spiro Compounds / chemistry
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Spiro Compounds / pharmacology*
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Cholinesterase Inhibitors
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Indoles
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Oxindoles
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Piperidines
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Pyrroles
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Spiro Compounds
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2-oxindole
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piperidine
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Butyrylcholinesterase
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Cholinesterases