title: Solanocapsine derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies.
abstract: 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.
authors.affiliation: INFIQC-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA Córdoba, Argentina. Electronic address: manuelagarcia@fcq.unc.edu.ar.
authors.forename: Manuela E
authors.initials: ME
authors.lastname: García
authors.affiliation: INFIQC-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA Córdoba, Argentina.
authors.forename: José L
authors.initials: JL
authors.lastname: Borioni
authors.affiliation: INQUISUR-CONICET, Departamento de Química, Universidad Nacional del Sur, B8000CPB Bahía Blanca, Argentina.
authors.forename: Valeria
authors.initials: V
authors.lastname: Cavallaro
authors.affiliation: INFIQC-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA Córdoba, Argentina.
authors.forename: Marcelo
authors.initials: M
authors.lastname: Puiatti
authors.affiliation: INFIQC-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA Córdoba, Argentina.
authors.forename: Adriana B
authors.initials: AB
authors.lastname: Pierini
authors.affiliation: INQUISUR-CONICET, Departamento de Química, Universidad Nacional del Sur, B8000CPB Bahía Blanca, Argentina.
authors.forename: Ana P
authors.initials: AP
authors.lastname: Murray
authors.affiliation: INFIQC-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA Córdoba, Argentina. Electronic address: penenory@fcq.unc.edu.ar.
authors.forename: Alicia B
authors.initials: AB
authors.lastname: Peñéñory
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism*; D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004593:Electrophorus; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000470:Alkaloids; D002800:Cholinesterase Inhibitors; D013256:Steroids; D000110:Acetylcholinesterase
keywords: Acetylcholinesterase inhibitors; Solanocapsine derivatives; Solanum pseudocapsicum; Steroidal alkaloids; Structure–activity relationship