A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors

Autores
Garro Martinez, Juan Ceferino; Duchowicz, Pablo Román; Estrada, Mario Rinaldo; Castro, Eduardo Alberto
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A quantitative structure activity relationship analysis was applied to a library of 51 benzylacetamide derivatives with anticonvulsant activity. The molecular structures of 51 compounds were optimized with the Semiempirical Method PM6 (Parametric Method-6) included in the MOPAC2009 software. The optimized structures of all the examined compounds were represented by 1497 DRAGON-type descriptors. Using multiple linear regression (MLR), the influence of constitutional, topological, electronic, physicochemical and quantum molecular descriptors on the activity was investigated. The validation of models were performed through the leave-one-out cross technique in conjunction with external validation. From different types of molecular descriptors, six new QSAR models were developed. The models using 0D descriptors (constitutional descriptors) and quantum descriptors do not have high statistical quality. The combination of 2D and 3D descriptors produce a model of high predictive quality (Rcal= 0.888; Scal= 0.195; Rval= 0.814; Sval=0.431; Rloo=0.867; Sloo=0.212). Results show the important role of electronic and topologic features of molecules on their anticonvulsant activity in relative to constitutional parameters.
Fil: Garro Martinez, Juan Ceferino. Universidad Nacional de San Luis. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Duchowicz, Pablo Román. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Nacional de La Plata; Argentina
Fil: Estrada, Mario Rinaldo. Universidad Nacional de San Luis. Departamento de Química; Argentina
Fil: Castro, Eduardo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Nacional de La Plata; Argentina
Materia
Qsar Theory
Acetamido-N-Benzylacetamide Derivatives
Flexible Descriptors
Dragon-Type
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:11336/5228
Acceder
id CONICETDig_31a5b2836266a95492b3d44786d36122
oai_identifier_str oai:ri.conicet.gov.ar:11336/5228
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular DescriptorsGarro Martinez, Juan CeferinoDuchowicz, Pablo RománEstrada, Mario RinaldoCastro, Eduardo AlbertoQsar TheoryAcetamido-N-Benzylacetamide DerivativesFlexible DescriptorsDragon-Typehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A quantitative structure activity relationship analysis was applied to a library of 51 benzylacetamide derivatives with anticonvulsant activity. The molecular structures of 51 compounds were optimized with the Semiempirical Method PM6 (Parametric Method-6) included in the MOPAC2009 software. The optimized structures of all the examined compounds were represented by 1497 DRAGON-type descriptors. Using multiple linear regression (MLR), the influence of constitutional, topological, electronic, physicochemical and quantum molecular descriptors on the activity was investigated. The validation of models were performed through the leave-one-out cross technique in conjunction with external validation. From different types of molecular descriptors, six new QSAR models were developed. The models using 0D descriptors (constitutional descriptors) and quantum descriptors do not have high statistical quality. The combination of 2D and 3D descriptors produce a model of high predictive quality (Rcal= 0.888; Scal= 0.195; Rval= 0.814; Sval=0.431; Rloo=0.867; Sloo=0.212). Results show the important role of electronic and topologic features of molecules on their anticonvulsant activity in relative to constitutional parameters.Fil: Garro Martinez, Juan Ceferino. Universidad Nacional de San Luis. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Duchowicz, Pablo Román. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Nacional de La Plata; ArgentinaFil: Estrada, Mario Rinaldo. Universidad Nacional de San Luis. Departamento de Química; ArgentinaFil: Castro, Eduardo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Nacional de La Plata; ArgentinaUniv Kragujevac2012-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/5228Garro Martinez, Juan Ceferino; Duchowicz, Pablo Román; Estrada, Mario Rinaldo; Castro, Eduardo Alberto; A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors; Univ Kragujevac; Match-communications In Mathematical And In Computer Chemistry; 67; 3; 1-2012; 745-7580340-6253enginfo:eu-repo/semantics/altIdentifier/url/http://match.pmf.kg.ac.rs/electronic_versions/Match67/n3/match67n3_745-758.pdfinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:43:37Zoai:ri.conicet.gov.ar:11336/5228instacron: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:34982025-10-15 15:43:37.941CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors
title A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors
spellingShingle A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors
Garro Martinez, Juan Ceferino
Qsar Theory
Acetamido-N-Benzylacetamide Derivatives
Flexible Descriptors
Dragon-Type
title_short A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors
title_full A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors
title_fullStr A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors
title_full_unstemmed A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors
title_sort A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors
dc.creator.none.fl_str_mv Garro Martinez, Juan Ceferino
Duchowicz, Pablo Román
Estrada, Mario Rinaldo
Castro, Eduardo Alberto
author Garro Martinez, Juan Ceferino
author_facet Garro Martinez, Juan Ceferino
Duchowicz, Pablo Román
Estrada, Mario Rinaldo
Castro, Eduardo Alberto
author_role author
author2 Duchowicz, Pablo Román
Estrada, Mario Rinaldo
Castro, Eduardo Alberto
author2_role author
author
author
dc.subject.none.fl_str_mv Qsar Theory
Acetamido-N-Benzylacetamide Derivatives
Flexible Descriptors
Dragon-Type
topic Qsar Theory
Acetamido-N-Benzylacetamide Derivatives
Flexible Descriptors
Dragon-Type
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A quantitative structure activity relationship analysis was applied to a library of 51 benzylacetamide derivatives with anticonvulsant activity. The molecular structures of 51 compounds were optimized with the Semiempirical Method PM6 (Parametric Method-6) included in the MOPAC2009 software. The optimized structures of all the examined compounds were represented by 1497 DRAGON-type descriptors. Using multiple linear regression (MLR), the influence of constitutional, topological, electronic, physicochemical and quantum molecular descriptors on the activity was investigated. The validation of models were performed through the leave-one-out cross technique in conjunction with external validation. From different types of molecular descriptors, six new QSAR models were developed. The models using 0D descriptors (constitutional descriptors) and quantum descriptors do not have high statistical quality. The combination of 2D and 3D descriptors produce a model of high predictive quality (Rcal= 0.888; Scal= 0.195; Rval= 0.814; Sval=0.431; Rloo=0.867; Sloo=0.212). Results show the important role of electronic and topologic features of molecules on their anticonvulsant activity in relative to constitutional parameters.
Fil: Garro Martinez, Juan Ceferino. Universidad Nacional de San Luis. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Duchowicz, Pablo Román. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Nacional de La Plata; Argentina
Fil: Estrada, Mario Rinaldo. Universidad Nacional de San Luis. Departamento de Química; Argentina
Fil: Castro, Eduardo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad Nacional de La Plata; Argentina
description A quantitative structure activity relationship analysis was applied to a library of 51 benzylacetamide derivatives with anticonvulsant activity. The molecular structures of 51 compounds were optimized with the Semiempirical Method PM6 (Parametric Method-6) included in the MOPAC2009 software. The optimized structures of all the examined compounds were represented by 1497 DRAGON-type descriptors. Using multiple linear regression (MLR), the influence of constitutional, topological, electronic, physicochemical and quantum molecular descriptors on the activity was investigated. The validation of models were performed through the leave-one-out cross technique in conjunction with external validation. From different types of molecular descriptors, six new QSAR models were developed. The models using 0D descriptors (constitutional descriptors) and quantum descriptors do not have high statistical quality. The combination of 2D and 3D descriptors produce a model of high predictive quality (Rcal= 0.888; Scal= 0.195; Rval= 0.814; Sval=0.431; Rloo=0.867; Sloo=0.212). Results show the important role of electronic and topologic features of molecules on their anticonvulsant activity in relative to constitutional parameters.
publishDate 2012
dc.date.none.fl_str_mv 2012-01
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/11336/5228
Garro Martinez, Juan Ceferino; Duchowicz, Pablo Román; Estrada, Mario Rinaldo; Castro, Eduardo Alberto; A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors; Univ Kragujevac; Match-communications In Mathematical And In Computer Chemistry; 67; 3; 1-2012; 745-758
0340-6253
url http://hdl.handle.net/11336/5228
identifier_str_mv Garro Martinez, Juan Ceferino; Duchowicz, Pablo Román; Estrada, Mario Rinaldo; Castro, Eduardo Alberto; A Multivariate QSAR Study on the Anticonvulsant Activity of Acetamido-N-Benzylacetamide Derivatives. Influence of Different Molecular Descriptors; Univ Kragujevac; Match-communications In Mathematical And In Computer Chemistry; 67; 3; 1-2012; 745-758
0340-6253
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://match.pmf.kg.ac.rs/electronic_versions/Match67/n3/match67n3_745-758.pdf
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
application/pdf
dc.publisher.none.fl_str_mv Univ Kragujevac
publisher.none.fl_str_mv Univ Kragujevac
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_ 1846083541106950144
score 13.22299

Publicaciones similares