In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity

Autores
Garro Martinez, Juan Ceferino; Vega Hissi, Esteban Gabriel; Andrada, Matias Fernando; Spedaletti, Cesar; Estrada, Mario R.
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A study about the relationship between molecular properties of open-chain enaminones and their anticonvulsant activity is presented in this paper. Geometry optimizations of the enaminones were performed at HF and DFT/B3LYP levels of theory using 6-31+G(d) basis set. The HOMO and LUMO energies were obtained at the same level of theory. The solvent effect was studied through IPCM. A Natural Bond Orbital (NBO) analysis was performed to analyze the possible association between the stability and the intramolecular hydrogen bond interaction energies. The stability order of the isomers in gas phase was the following: cis-1 > trans-4 > cis-2 > trans-3. The IPCM method showed that the trans-3 isomers are more stable that the cis-2 when the solvent effect was taken into account. Two important intramolecular hydrogen bonds were found by NBO analysis. According to our findings, these interactions could affect the activity of the two most stable isomers (cis-1 and trans-4). By contrast, trans-3 isomers did not present this type of interaction. Therefore, the latter isomers have a large flexibility and can adopt a conformation similar to the conformation of active ringed-enaminones. In addition, HOMO and LUMO energies suggested that the trans-3 isomers could be the most reactive species.
Fil: Garro Martinez, Juan Ceferino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Vega Hissi, Esteban Gabriel. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Andrada, Matias Fernando. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Catedra de Quimica Fisica; Argentina
Fil: Spedaletti, Cesar. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Estrada, Mario R.. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Materia
Open-Chain Enaminones
Anticonvulsant Activity
Structure-Activity Relationship
Active Conformation
Ab Initio
Nbo Analysis
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:11336/6981
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/6981
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activityGarro Martinez, Juan CeferinoVega Hissi, Esteban GabrielAndrada, Matias FernandoSpedaletti, CesarEstrada, Mario R.Open-Chain EnaminonesAnticonvulsant ActivityStructure-Activity RelationshipActive ConformationAb InitioNbo Analysishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A study about the relationship between molecular properties of open-chain enaminones and their anticonvulsant activity is presented in this paper. Geometry optimizations of the enaminones were performed at HF and DFT/B3LYP levels of theory using 6-31+G(d) basis set. The HOMO and LUMO energies were obtained at the same level of theory. The solvent effect was studied through IPCM. A Natural Bond Orbital (NBO) analysis was performed to analyze the possible association between the stability and the intramolecular hydrogen bond interaction energies. The stability order of the isomers in gas phase was the following: cis-1 > trans-4 > cis-2 > trans-3. The IPCM method showed that the trans-3 isomers are more stable that the cis-2 when the solvent effect was taken into account. Two important intramolecular hydrogen bonds were found by NBO analysis. According to our findings, these interactions could affect the activity of the two most stable isomers (cis-1 and trans-4). By contrast, trans-3 isomers did not present this type of interaction. Therefore, the latter isomers have a large flexibility and can adopt a conformation similar to the conformation of active ringed-enaminones. In addition, HOMO and LUMO energies suggested that the trans-3 isomers could be the most reactive species.Fil: Garro Martinez, Juan Ceferino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; ArgentinaFil: Vega Hissi, Esteban Gabriel. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; ArgentinaFil: Andrada, Matias Fernando. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Catedra de Quimica Fisica; ArgentinaFil: Spedaletti, Cesar. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; ArgentinaFil: Estrada, Mario R.. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; ArgentinaSpringer2014-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/zipapplication/pdfhttp://hdl.handle.net/11336/6981Garro Martinez, Juan Ceferino; Vega Hissi, Esteban Gabriel; Andrada, Matias Fernando; Spedaletti, Cesar; Estrada, Mario R.; In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity; Springer; Medicinal Chemistry Research; 23; 5; 5-2014; 2528-25351054-2523enginfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/url/http://dx.oi.org/10.1007/s00044-013-0783-1info:eu-repo/semantics/altIdentifier/url/http://link.springer.com/article/10.1007/s00044-013-0783-1info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:23:02Zoai:ri.conicet.gov.ar:11336/6981instacron: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 14:23:03.06CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity
title In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity
spellingShingle In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity
Garro Martinez, Juan Ceferino
Open-Chain Enaminones
Anticonvulsant Activity
Structure-Activity Relationship
Active Conformation
Ab Initio
Nbo Analysis
title_short In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity
title_full In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity
title_fullStr In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity
title_full_unstemmed In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity
title_sort In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity
dc.creator.none.fl_str_mv Garro Martinez, Juan Ceferino
Vega Hissi, Esteban Gabriel
Andrada, Matias Fernando
Spedaletti, Cesar
Estrada, Mario R.
author Garro Martinez, Juan Ceferino
author_facet Garro Martinez, Juan Ceferino
Vega Hissi, Esteban Gabriel
Andrada, Matias Fernando
Spedaletti, Cesar
Estrada, Mario R.
author_role author
author2 Vega Hissi, Esteban Gabriel
Andrada, Matias Fernando
Spedaletti, Cesar
Estrada, Mario R.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Open-Chain Enaminones
Anticonvulsant Activity
Structure-Activity Relationship
Active Conformation
Ab Initio
Nbo Analysis
topic Open-Chain Enaminones
Anticonvulsant Activity
Structure-Activity Relationship
Active Conformation
Ab Initio
Nbo Analysis
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 study about the relationship between molecular properties of open-chain enaminones and their anticonvulsant activity is presented in this paper. Geometry optimizations of the enaminones were performed at HF and DFT/B3LYP levels of theory using 6-31+G(d) basis set. The HOMO and LUMO energies were obtained at the same level of theory. The solvent effect was studied through IPCM. A Natural Bond Orbital (NBO) analysis was performed to analyze the possible association between the stability and the intramolecular hydrogen bond interaction energies. The stability order of the isomers in gas phase was the following: cis-1 > trans-4 > cis-2 > trans-3. The IPCM method showed that the trans-3 isomers are more stable that the cis-2 when the solvent effect was taken into account. Two important intramolecular hydrogen bonds were found by NBO analysis. According to our findings, these interactions could affect the activity of the two most stable isomers (cis-1 and trans-4). By contrast, trans-3 isomers did not present this type of interaction. Therefore, the latter isomers have a large flexibility and can adopt a conformation similar to the conformation of active ringed-enaminones. In addition, HOMO and LUMO energies suggested that the trans-3 isomers could be the most reactive species.
Fil: Garro Martinez, Juan Ceferino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Vega Hissi, Esteban Gabriel. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Andrada, Matias Fernando. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Catedra de Quimica Fisica; Argentina
Fil: Spedaletti, Cesar. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
Fil: Estrada, Mario R.. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica. Area de Quimica Fisica; Argentina
description A study about the relationship between molecular properties of open-chain enaminones and their anticonvulsant activity is presented in this paper. Geometry optimizations of the enaminones were performed at HF and DFT/B3LYP levels of theory using 6-31+G(d) basis set. The HOMO and LUMO energies were obtained at the same level of theory. The solvent effect was studied through IPCM. A Natural Bond Orbital (NBO) analysis was performed to analyze the possible association between the stability and the intramolecular hydrogen bond interaction energies. The stability order of the isomers in gas phase was the following: cis-1 > trans-4 > cis-2 > trans-3. The IPCM method showed that the trans-3 isomers are more stable that the cis-2 when the solvent effect was taken into account. Two important intramolecular hydrogen bonds were found by NBO analysis. According to our findings, these interactions could affect the activity of the two most stable isomers (cis-1 and trans-4). By contrast, trans-3 isomers did not present this type of interaction. Therefore, the latter isomers have a large flexibility and can adopt a conformation similar to the conformation of active ringed-enaminones. In addition, HOMO and LUMO energies suggested that the trans-3 isomers could be the most reactive species.
publishDate 2014
dc.date.none.fl_str_mv 2014-05
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/11336/6981
Garro Martinez, Juan Ceferino; Vega Hissi, Esteban Gabriel; Andrada, Matias Fernando; Spedaletti, Cesar; Estrada, Mario R.; In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity; Springer; Medicinal Chemistry Research; 23; 5; 5-2014; 2528-2535
1054-2523
url http://hdl.handle.net/11336/6981
identifier_str_mv Garro Martinez, Juan Ceferino; Vega Hissi, Esteban Gabriel; Andrada, Matias Fernando; Spedaletti, Cesar; Estrada, Mario R.; In silico identification of the active conformation of open-chain enaminoes with anticonvulsant activity; Springer; Medicinal Chemistry Research; 23; 5; 5-2014; 2528-2535
1054-2523
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/url/http://dx.oi.org/10.1007/s00044-013-0783-1
info:eu-repo/semantics/altIdentifier/url/http://link.springer.com/article/10.1007/s00044-013-0783-1
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/zip
application/pdf
dc.publisher.none.fl_str_mv Springer
publisher.none.fl_str_mv Springer
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 13.22299

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