Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation

Autores
Hudcová, Anna; Kroutil, Ales; Kubínová, Renata; Garro, Adriana; Gutierrez, Lucas Joel; Enriz, Ricardo Daniel; Oravec, Michal; Csöllei, Jozef
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Neurodegenerative diseases in which the decrease of the acetylcholine is observed are growing worldwide. In the present study, a series of new arylaminopropanone derivatives with N-phenylcarbamate moiety (1-16) were prepared as potential acetylcholinesterase and butyrylcholinesterase inhibitors. In vitro enzyme assays were performed; the results are expressed as a percentage of inhibition and the IC50 values. The inhibitory activities were compared with reference drugs galantamine and rivastigmine showing piperidine derivatives (1-3) as the most potent. A possible mechanism of action for these compounds was determined from a molecular modelling study by using combined techniques of docking, molecular dynamics simulations and quantum mechanics calculations.
Fil: Hudcová, Anna. University Of Veterinary And Pharmaceutical Sciences; República Checa
Fil: Kroutil, Ales. University Of Veterinary And Pharmaceutical Sciences; República Checa
Fil: Kubínová, Renata. University Of Veterinary And Pharmaceutical Sciences; República Checa
Fil: Garro, Adriana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Gutierrez, Lucas Joel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Oravec, Michal. Global Change Research Institute; República Checa
Fil: Csöllei, Jozef. University Of Veterinary And Pharmaceutical Sciences; República Checa
Materia
ACETYLCHOLINESTERASE
ARYLAMINOPROPANONE
BUTYRYLCHOLINESTERASE
ENZYME ASSAYS
MOLECULAR MODELLING
N-PHENYLCARBAMATE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/145013
Acceder
id CONICETDig_38d5f625a092e471a489f6e75cfe20f5
oai_identifier_str oai:ri.conicet.gov.ar:11336/145013
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological EvaluationHudcová, AnnaKroutil, AlesKubínová, RenataGarro, AdrianaGutierrez, Lucas JoelEnriz, Ricardo DanielOravec, MichalCsöllei, JozefACETYLCHOLINESTERASEARYLAMINOPROPANONEBUTYRYLCHOLINESTERASEENZYME ASSAYSMOLECULAR MODELLINGN-PHENYLCARBAMATEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Neurodegenerative diseases in which the decrease of the acetylcholine is observed are growing worldwide. In the present study, a series of new arylaminopropanone derivatives with N-phenylcarbamate moiety (1-16) were prepared as potential acetylcholinesterase and butyrylcholinesterase inhibitors. In vitro enzyme assays were performed; the results are expressed as a percentage of inhibition and the IC50 values. The inhibitory activities were compared with reference drugs galantamine and rivastigmine showing piperidine derivatives (1-3) as the most potent. A possible mechanism of action for these compounds was determined from a molecular modelling study by using combined techniques of docking, molecular dynamics simulations and quantum mechanics calculations.Fil: Hudcová, Anna. University Of Veterinary And Pharmaceutical Sciences; República ChecaFil: Kroutil, Ales. University Of Veterinary And Pharmaceutical Sciences; República ChecaFil: Kubínová, Renata. University Of Veterinary And Pharmaceutical Sciences; República ChecaFil: Garro, Adriana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Gutierrez, Lucas Joel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Oravec, Michal. Global Change Research Institute; República ChecaFil: Csöllei, Jozef. University Of Veterinary And Pharmaceutical Sciences; República ChecaMolecular Diversity Preservation International2020-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/145013Hudcová, Anna; Kroutil, Ales; Kubínová, Renata; Garro, Adriana; Gutierrez, Lucas Joel; et al.; Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation; Molecular Diversity Preservation International; Molecules; 25; 7; 4-2020; 1-171420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/25/7/1751info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules25071751info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T09:40:03Zoai:ri.conicet.gov.ar:11336/145013instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-05 09:40:03.423CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation
title Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation
spellingShingle Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation
Hudcová, Anna
ACETYLCHOLINESTERASE
ARYLAMINOPROPANONE
BUTYRYLCHOLINESTERASE
ENZYME ASSAYS
MOLECULAR MODELLING
N-PHENYLCARBAMATE
title_short Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation
title_full Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation
title_fullStr Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation
title_full_unstemmed Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation
title_sort Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation
dc.creator.none.fl_str_mv Hudcová, Anna
Kroutil, Ales
Kubínová, Renata
Garro, Adriana
Gutierrez, Lucas Joel
Enriz, Ricardo Daniel
Oravec, Michal
Csöllei, Jozef
author Hudcová, Anna
author_facet Hudcová, Anna
Kroutil, Ales
Kubínová, Renata
Garro, Adriana
Gutierrez, Lucas Joel
Enriz, Ricardo Daniel
Oravec, Michal
Csöllei, Jozef
author_role author
author2 Kroutil, Ales
Kubínová, Renata
Garro, Adriana
Gutierrez, Lucas Joel
Enriz, Ricardo Daniel
Oravec, Michal
Csöllei, Jozef
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ACETYLCHOLINESTERASE
ARYLAMINOPROPANONE
BUTYRYLCHOLINESTERASE
ENZYME ASSAYS
MOLECULAR MODELLING
N-PHENYLCARBAMATE
topic ACETYLCHOLINESTERASE
ARYLAMINOPROPANONE
BUTYRYLCHOLINESTERASE
ENZYME ASSAYS
MOLECULAR MODELLING
N-PHENYLCARBAMATE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Neurodegenerative diseases in which the decrease of the acetylcholine is observed are growing worldwide. In the present study, a series of new arylaminopropanone derivatives with N-phenylcarbamate moiety (1-16) were prepared as potential acetylcholinesterase and butyrylcholinesterase inhibitors. In vitro enzyme assays were performed; the results are expressed as a percentage of inhibition and the IC50 values. The inhibitory activities were compared with reference drugs galantamine and rivastigmine showing piperidine derivatives (1-3) as the most potent. A possible mechanism of action for these compounds was determined from a molecular modelling study by using combined techniques of docking, molecular dynamics simulations and quantum mechanics calculations.
Fil: Hudcová, Anna. University Of Veterinary And Pharmaceutical Sciences; República Checa
Fil: Kroutil, Ales. University Of Veterinary And Pharmaceutical Sciences; República Checa
Fil: Kubínová, Renata. University Of Veterinary And Pharmaceutical Sciences; República Checa
Fil: Garro, Adriana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Gutierrez, Lucas Joel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Oravec, Michal. Global Change Research Institute; República Checa
Fil: Csöllei, Jozef. University Of Veterinary And Pharmaceutical Sciences; República Checa
description Neurodegenerative diseases in which the decrease of the acetylcholine is observed are growing worldwide. In the present study, a series of new arylaminopropanone derivatives with N-phenylcarbamate moiety (1-16) were prepared as potential acetylcholinesterase and butyrylcholinesterase inhibitors. In vitro enzyme assays were performed; the results are expressed as a percentage of inhibition and the IC50 values. The inhibitory activities were compared with reference drugs galantamine and rivastigmine showing piperidine derivatives (1-3) as the most potent. A possible mechanism of action for these compounds was determined from a molecular modelling study by using combined techniques of docking, molecular dynamics simulations and quantum mechanics calculations.
publishDate 2020
dc.date.none.fl_str_mv 2020-04
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/145013
Hudcová, Anna; Kroutil, Ales; Kubínová, Renata; Garro, Adriana; Gutierrez, Lucas Joel; et al.; Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation; Molecular Diversity Preservation International; Molecules; 25; 7; 4-2020; 1-17
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/145013
identifier_str_mv Hudcová, Anna; Kroutil, Ales; Kubínová, Renata; Garro, Adriana; Gutierrez, Lucas Joel; et al.; Arylaminopropanone Derivatives as Potential Cholinesterase Inhibitors: Synthesis, Docking Study and Biological Evaluation; Molecular Diversity Preservation International; Molecules; 25; 7; 4-2020; 1-17
1420-3049
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/25/7/1751
info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules25071751
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1847976934559973376
score 13.087074

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