Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary...

Autores: Padrtova, Tereza; Marvanova, Pavlina; Odehnalova, Klara; Kubinova, Renata; Parravicini, Oscar; Garro, Adriana; Enriz, Ricardo Daniel; Humpa, Otakar; Oravec, Michal; Mokry, Petr
Año de publicación: 2017
Idioma: inglés
Tipo de recurso: artículo
Estado: versión publicada
Descripción: Tertiary amines 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxycarbonyl)amino]benzoates and their quaternary ammonium salts were synthesized. The final step of synthesis of quaternary ammonium salts was carried out by microwave-assisted synthesis. Software-calculated data provided the background needed to compare fifteen new resulting compounds by their physicochemical properties. The acid dissociation constant (pKa) and lipophilicity index (log P) of tertiary amines were determined; while quaternary ammonium salts were characterized by software-calculated lipophilicity index and surface tension. Biological evaluation aimed at testing acetylcholinesterase and butyrylcholinesterase-inhibiting activity of synthesized compounds. A possible mechanism of action of these compounds was determined by molecular modelling study using combined techniques of docking; molecular dynamics simulations and quantum mechanics calculations.
Fil: Padrtova, Tereza. University of Veterinary and Pharmaceutical Sciences Brno ; República Checa
Fil: Marvanova, Pavlina. University of Veterinary and Pharmaceutical Sciences Brno ; República Checa
Fil: Odehnalova, Klara. University of Veterinary and Pharmaceutical Sciences Brno ; República Checa
Fil: Kubinova, Renata. University of Veterinary and Pharmaceutical Sciences Brno ; República Checa
Fil: Parravicini, Oscar. 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: 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: 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: Humpa, Otakar. Masaryk University; República Checa
Fil: Oravec, Michal. Global Change Research Institute CAS; República Checa
Fil: Mokry, Petr. University of Veterinary and Pharmaceutical Sciences Brno ; República Checa
Materia: ACETYLCHOLINESTERASE
ARYLCARBONYLOXYAMINOPROPANOLS
BUTYRYLCHOLINESTERASE
QUATERNARY AMMONIUM SALTS
TERTIARY AMINES
Nivel de accesibilidad: acceso abierto
Condiciones de uso: https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
Institución: Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador: oai:ri.conicet.gov.ar:11336/67221

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network_acronym_str	CONICETDig
repository_id_str	3498
network_name_str	CONICET Digital (CONICET)
spelling	Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium saltsPadrtova, TerezaMarvanova, PavlinaOdehnalova, KlaraKubinova, RenataParravicini, OscarGarro, AdrianaEnriz, Ricardo DanielHumpa, OtakarOravec, MichalMokry, PetrACETYLCHOLINESTERASEARYLCARBONYLOXYAMINOPROPANOLSBUTYRYLCHOLINESTERASEQUATERNARY AMMONIUM SALTSTERTIARY AMINEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Tertiary amines 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxycarbonyl)amino]benzoates and their quaternary ammonium salts were synthesized. The final step of synthesis of quaternary ammonium salts was carried out by microwave-assisted synthesis. Software-calculated data provided the background needed to compare fifteen new resulting compounds by their physicochemical properties. The acid dissociation constant (pKa) and lipophilicity index (log P) of tertiary amines were determined; while quaternary ammonium salts were characterized by software-calculated lipophilicity index and surface tension. Biological evaluation aimed at testing acetylcholinesterase and butyrylcholinesterase-inhibiting activity of synthesized compounds. A possible mechanism of action of these compounds was determined by molecular modelling study using combined techniques of docking; molecular dynamics simulations and quantum mechanics calculations.Fil: Padrtova, Tereza. University of Veterinary and Pharmaceutical Sciences Brno ; República ChecaFil: Marvanova, Pavlina. University of Veterinary and Pharmaceutical Sciences Brno ; República ChecaFil: Odehnalova, Klara. University of Veterinary and Pharmaceutical Sciences Brno ; República ChecaFil: Kubinova, Renata. University of Veterinary and Pharmaceutical Sciences Brno ; República ChecaFil: Parravicini, Oscar. 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: 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: 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: Humpa, Otakar. Masaryk University; República ChecaFil: Oravec, Michal. Global Change Research Institute CAS; República ChecaFil: Mokry, Petr. University of Veterinary and Pharmaceutical Sciences Brno ; República ChecaMolecular Diversity Preservation International2017-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/67221Padrtova, Tereza; Marvanova, Pavlina; Odehnalova, Klara; Kubinova, Renata; Parravicini, Oscar; et al.; Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts; Molecular Diversity Preservation International; Molecules; 22; 12; 12-2017; 1-211420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/molecules22122048info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/22/12/2048info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:07:40Zoai:ri.conicet.gov.ar:11336/67221instacron: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:34982025-09-03 10:07:40.685CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv	Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts
title	Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts
spellingShingle	Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts Padrtova, Tereza ACETYLCHOLINESTERASE ARYLCARBONYLOXYAMINOPROPANOLS BUTYRYLCHOLINESTERASE QUATERNARY AMMONIUM SALTS TERTIARY AMINES
title_short	Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts
title_full	Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts
title_fullStr	Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts
title_full_unstemmed	Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts
title_sort	Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts
dc.creator.none.fl_str_mv	Padrtova, Tereza Marvanova, Pavlina Odehnalova, Klara Kubinova, Renata Parravicini, Oscar Garro, Adriana Enriz, Ricardo Daniel Humpa, Otakar Oravec, Michal Mokry, Petr
author	Padrtova, Tereza
author_facet	Padrtova, Tereza Marvanova, Pavlina Odehnalova, Klara Kubinova, Renata Parravicini, Oscar Garro, Adriana Enriz, Ricardo Daniel Humpa, Otakar Oravec, Michal Mokry, Petr
author_role	author
author2	Marvanova, Pavlina Odehnalova, Klara Kubinova, Renata Parravicini, Oscar Garro, Adriana Enriz, Ricardo Daniel Humpa, Otakar Oravec, Michal Mokry, Petr
author2_role	author author author author author author author author author
dc.subject.none.fl_str_mv	ACETYLCHOLINESTERASE ARYLCARBONYLOXYAMINOPROPANOLS BUTYRYLCHOLINESTERASE QUATERNARY AMMONIUM SALTS TERTIARY AMINES
topic	ACETYLCHOLINESTERASE ARYLCARBONYLOXYAMINOPROPANOLS BUTYRYLCHOLINESTERASE QUATERNARY AMMONIUM SALTS TERTIARY AMINES
purl_subject.fl_str_mv	https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv	Tertiary amines 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxycarbonyl)amino]benzoates and their quaternary ammonium salts were synthesized. The final step of synthesis of quaternary ammonium salts was carried out by microwave-assisted synthesis. Software-calculated data provided the background needed to compare fifteen new resulting compounds by their physicochemical properties. The acid dissociation constant (pKa) and lipophilicity index (log P) of tertiary amines were determined; while quaternary ammonium salts were characterized by software-calculated lipophilicity index and surface tension. Biological evaluation aimed at testing acetylcholinesterase and butyrylcholinesterase-inhibiting activity of synthesized compounds. A possible mechanism of action of these compounds was determined by molecular modelling study using combined techniques of docking; molecular dynamics simulations and quantum mechanics calculations. Fil: Padrtova, Tereza. University of Veterinary and Pharmaceutical Sciences Brno ; República Checa Fil: Marvanova, Pavlina. University of Veterinary and Pharmaceutical Sciences Brno ; República Checa Fil: Odehnalova, Klara. University of Veterinary and Pharmaceutical Sciences Brno ; República Checa Fil: Kubinova, Renata. University of Veterinary and Pharmaceutical Sciences Brno ; República Checa Fil: Parravicini, Oscar. 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: 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: 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: Humpa, Otakar. Masaryk University; República Checa Fil: Oravec, Michal. Global Change Research Institute CAS; República Checa Fil: Mokry, Petr. University of Veterinary and Pharmaceutical Sciences Brno ; República Checa
description	Tertiary amines 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxycarbonyl)amino]benzoates and their quaternary ammonium salts were synthesized. The final step of synthesis of quaternary ammonium salts was carried out by microwave-assisted synthesis. Software-calculated data provided the background needed to compare fifteen new resulting compounds by their physicochemical properties. The acid dissociation constant (pKa) and lipophilicity index (log P) of tertiary amines were determined; while quaternary ammonium salts were characterized by software-calculated lipophilicity index and surface tension. Biological evaluation aimed at testing acetylcholinesterase and butyrylcholinesterase-inhibiting activity of synthesized compounds. A possible mechanism of action of these compounds was determined by molecular modelling study using combined techniques of docking; molecular dynamics simulations and quantum mechanics calculations.
publishDate	2017
dc.date.none.fl_str_mv	2017-12
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/11336/67221 Padrtova, Tereza; Marvanova, Pavlina; Odehnalova, Klara; Kubinova, Renata; Parravicini, Oscar; et al.; Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts; Molecular Diversity Preservation International; Molecules; 22; 12; 12-2017; 1-21 1420-3049 CONICET Digital CONICET
url	http://hdl.handle.net/11336/67221
identifier_str_mv	Padrtova, Tereza; Marvanova, Pavlina; Odehnalova, Klara; Kubinova, Renata; Parravicini, Oscar; et al.; Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary ammonium salts; Molecular Diversity Preservation International; Molecules; 22; 12; 12-2017; 1-21 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/doi/10.3390/molecules22122048 info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/22/12/2048
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
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score	12.885934

Synthesis, analysis, cholinesterase-inhibiting activity and molecular modelling studies of 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxy-carbonyl)amino]benzoates and their quaternary...

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