Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives
Autor(a) principal: | |
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Data de Publicação: | 2016 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202312 |
Resumo: | A series of the new urea derivatives with antinociceptive activity has been chromatographically evaluated using reversed phase materials: Zorbax Extend-C18, Cogent UDC Cholesterol with organic-aqueous eluent systems with two organic modifiers (methanol and acetonitrile). The chromatographic lipophilicity parameters: log kw, S and φ0 were determined basing on linear relationship between log k values and concentration of organic mobile phase modifier. The structure-retention studies revealed that the retention mechanism for all studied urea derivatives is uniform for the proposed chromatographic systems. However, a few exceptions were noticed. Derivatives containing nonpolar substituents in the imidazole ring acted as outliers for cholesterol column. In turn, the derivative containing ester polar substituent acted as an outlier in conventional reversed-phase system. Quantitative relationships based on a wide set of established computational molecular descriptors and experimental chromatographic data were also developed. Through a systematic study, by using the principal component analysis, fragmental method KowWIN appeared to be the most powerful software to produce reliable estimations of experimental retention parameters obtained on cholesterol column. |
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Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivativesurea derivativesreversed-phase HPLClipophilicityprincipal component analysisA series of the new urea derivatives with antinociceptive activity has been chromatographically evaluated using reversed phase materials: Zorbax Extend-C18, Cogent UDC Cholesterol with organic-aqueous eluent systems with two organic modifiers (methanol and acetonitrile). The chromatographic lipophilicity parameters: log kw, S and φ0 were determined basing on linear relationship between log k values and concentration of organic mobile phase modifier. The structure-retention studies revealed that the retention mechanism for all studied urea derivatives is uniform for the proposed chromatographic systems. However, a few exceptions were noticed. Derivatives containing nonpolar substituents in the imidazole ring acted as outliers for cholesterol column. In turn, the derivative containing ester polar substituent acted as an outlier in conventional reversed-phase system. Quantitative relationships based on a wide set of established computational molecular descriptors and experimental chromatographic data were also developed. Through a systematic study, by using the principal component analysis, fragmental method KowWIN appeared to be the most powerful software to produce reliable estimations of experimental retention parameters obtained on cholesterol column.Sociedade Brasileira de Química2016-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202312Journal of the Brazilian Chemical Society v.27 n.12 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160128info:eu-repo/semantics/openAccessFlieger,JolantaTatarczak-Michalewska,MałgorzataKowalska,AnnaRządkowska,MarzenaSzacoń,ElżbietaKaczor,Agnieszka A.Matosiuk,Dariuszeng2016-12-01T00:00:00Zoai:scielo:S0103-50532016001202312Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2016-12-01T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives |
title |
Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives |
spellingShingle |
Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives Flieger,Jolanta urea derivatives reversed-phase HPLC lipophilicity principal component analysis |
title_short |
Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives |
title_full |
Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives |
title_fullStr |
Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives |
title_full_unstemmed |
Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives |
title_sort |
Fragmental Method KowWIN as the Powerful Tool for Prediction of Chromatographic Behavior of Novel Bioactive Urea Derivatives |
author |
Flieger,Jolanta |
author_facet |
Flieger,Jolanta Tatarczak-Michalewska,Małgorzata Kowalska,Anna Rządkowska,Marzena Szacoń,Elżbieta Kaczor,Agnieszka A. Matosiuk,Dariusz |
author_role |
author |
author2 |
Tatarczak-Michalewska,Małgorzata Kowalska,Anna Rządkowska,Marzena Szacoń,Elżbieta Kaczor,Agnieszka A. Matosiuk,Dariusz |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
Flieger,Jolanta Tatarczak-Michalewska,Małgorzata Kowalska,Anna Rządkowska,Marzena Szacoń,Elżbieta Kaczor,Agnieszka A. Matosiuk,Dariusz |
dc.subject.por.fl_str_mv |
urea derivatives reversed-phase HPLC lipophilicity principal component analysis |
topic |
urea derivatives reversed-phase HPLC lipophilicity principal component analysis |
description |
A series of the new urea derivatives with antinociceptive activity has been chromatographically evaluated using reversed phase materials: Zorbax Extend-C18, Cogent UDC Cholesterol with organic-aqueous eluent systems with two organic modifiers (methanol and acetonitrile). The chromatographic lipophilicity parameters: log kw, S and φ0 were determined basing on linear relationship between log k values and concentration of organic mobile phase modifier. The structure-retention studies revealed that the retention mechanism for all studied urea derivatives is uniform for the proposed chromatographic systems. However, a few exceptions were noticed. Derivatives containing nonpolar substituents in the imidazole ring acted as outliers for cholesterol column. In turn, the derivative containing ester polar substituent acted as an outlier in conventional reversed-phase system. Quantitative relationships based on a wide set of established computational molecular descriptors and experimental chromatographic data were also developed. Through a systematic study, by using the principal component analysis, fragmental method KowWIN appeared to be the most powerful software to produce reliable estimations of experimental retention parameters obtained on cholesterol column. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016-12-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202312 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202312 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.5935/0103-5053.20160128 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.27 n.12 2016 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318179100393472 |