Solanocapsine derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies

[Display omitted] •Solanocapsine, a steroidal alkaloid was isolated from Solanum pseudocapsicum L.•A set of solanocapsine chemical derivatives was prepared.•Acetylcholinesterase inhibitory activity of all compounds was examined.•Some structure–activity relationships were established.•Interactions wi...

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Veröffentlicht in:Steroids 2015-12, Vol.104, p.95-110
Hauptverfasser: García, Manuela E., Borioni, José L., Cavallaro, Valeria, Puiatti, Marcelo, Pierini, Adriana B., Murray, Ana P., Peñéñory, Alicia B.
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container_end_page 110
container_issue
container_start_page 95
container_title Steroids
container_volume 104
creator García, Manuela E.
Borioni, José L.
Cavallaro, Valeria
Puiatti, Marcelo
Pierini, Adriana B.
Murray, Ana P.
Peñéñory, Alicia B.
description [Display omitted] •Solanocapsine, a steroidal alkaloid was isolated from Solanum pseudocapsicum L.•A set of solanocapsine chemical derivatives was prepared.•Acetylcholinesterase inhibitory activity of all compounds was examined.•Some structure–activity relationships were established.•Interactions with the enzyme and binding conformations were evaluated. The investigation of natural products in medicinal chemistry is essential today. In this context, acetylcholinesterase (AChE) inhibitors comprise one type of the compounds most actively studied in the search for an effective treatment of symptoms of Alzheimer’s disease. This work describes the isolation of a natural compound, solanocapsine, the preparation of its chemical derivatives, the evaluation of AChE inhibitory activity, and the structure–activity analysis of relevant cases. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different reactive parts of the parent molecule. A theoretical study was also carried out into the binding mode of representative compounds to the enzyme through molecular modeling. The biological properties of the series were investigated. Through this study valuable information was obtained of steroidal alkaloid-type compounds as a starting point for the synthesis of AChE inhibitors.
doi_str_mv 10.1016/j.steroids.2015.09.001
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The investigation of natural products in medicinal chemistry is essential today. In this context, acetylcholinesterase (AChE) inhibitors comprise one type of the compounds most actively studied in the search for an effective treatment of symptoms of Alzheimer’s disease. This work describes the isolation of a natural compound, solanocapsine, the preparation of its chemical derivatives, the evaluation of AChE inhibitory activity, and the structure–activity analysis of relevant cases. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different reactive parts of the parent molecule. A theoretical study was also carried out into the binding mode of representative compounds to the enzyme through molecular modeling. The biological properties of the series were investigated. 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The investigation of natural products in medicinal chemistry is essential today. In this context, acetylcholinesterase (AChE) inhibitors comprise one type of the compounds most actively studied in the search for an effective treatment of symptoms of Alzheimer’s disease. This work describes the isolation of a natural compound, solanocapsine, the preparation of its chemical derivatives, the evaluation of AChE inhibitory activity, and the structure–activity analysis of relevant cases. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different reactive parts of the parent molecule. A theoretical study was also carried out into the binding mode of representative compounds to the enzyme through molecular modeling. The biological properties of the series were investigated. 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subjects Acetylcholinesterase - metabolism
Acetylcholinesterase inhibitors
Alkaloids - chemical synthesis
Alkaloids - chemistry
Alkaloids - pharmacology
Animals
Cholinesterase Inhibitors - chemical synthesis
Cholinesterase Inhibitors - chemistry
Cholinesterase Inhibitors - pharmacology
Dose-Response Relationship, Drug
Electrophorus
Molecular Docking Simulation
Molecular Structure
Solanocapsine derivatives
Solanum pseudocapsicum
Steroidal alkaloids
Steroids - chemical synthesis
Steroids - chemistry
Steroids - pharmacology
Structure-Activity Relationship
title Solanocapsine derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies
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