Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers
Autor(a) principal: | |
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Data de Publicação: | 2017 |
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=S0103-50532017001102100 |
Resumo: | Heterocyclic oxime ethers play a significant role in organisms due to their biological activity. Lipophilicity is an important parameter that may affect biological activity of the compounds 1-(benzofuran-2-yl)ethan-1-one oxime and its nine biologically active ethers. The relationship between the structure and lipophilicity parameters (log kw values) of the ten compounds is here described. Reversed phase high performance liquid chromatography (RP-HPLC) method was used having methanol, 2-propanol and acetonitrile as organic modifiers of the mobile phases. Both experimental (log kw) and calculated (log P) parameters showed to be strongly positively correlated. The weakest correlation with all the data was for the log kw methanol. For all of analyzed compounds, log kw values are smaller than 5 (except for analyses carried out in methanol), and this result corresponds to the Lipinski’s rule in the range of lipophilicity. Therefore, in the case of their use as drugs, they will be probably active after oral application. |
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Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Etherslipophilicityoxime ethershigh-performance liquid chromatographybiological activityHeterocyclic oxime ethers play a significant role in organisms due to their biological activity. Lipophilicity is an important parameter that may affect biological activity of the compounds 1-(benzofuran-2-yl)ethan-1-one oxime and its nine biologically active ethers. The relationship between the structure and lipophilicity parameters (log kw values) of the ten compounds is here described. Reversed phase high performance liquid chromatography (RP-HPLC) method was used having methanol, 2-propanol and acetonitrile as organic modifiers of the mobile phases. Both experimental (log kw) and calculated (log P) parameters showed to be strongly positively correlated. The weakest correlation with all the data was for the log kw methanol. For all of analyzed compounds, log kw values are smaller than 5 (except for analyses carried out in methanol), and this result corresponds to the Lipinski’s rule in the range of lipophilicity. Therefore, in the case of their use as drugs, they will be probably active after oral application.Sociedade Brasileira de Química2017-11-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001102100Journal of the Brazilian Chemical Society v.28 n.11 2017reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20170055info:eu-repo/semantics/openAccessKosmalski,TomaszStudzińska,RenataRedka,MałgorzataPluskota,RobertModzelewska-Banachiewicz,Bożenaeng2017-10-26T00:00:00Zoai:scielo:S0103-50532017001102100Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2017-10-26T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers |
title |
Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers |
spellingShingle |
Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers Kosmalski,Tomasz lipophilicity oxime ethers high-performance liquid chromatography biological activity |
title_short |
Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers |
title_full |
Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers |
title_fullStr |
Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers |
title_full_unstemmed |
Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers |
title_sort |
Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers |
author |
Kosmalski,Tomasz |
author_facet |
Kosmalski,Tomasz Studzińska,Renata Redka,Małgorzata Pluskota,Robert Modzelewska-Banachiewicz,Bożena |
author_role |
author |
author2 |
Studzińska,Renata Redka,Małgorzata Pluskota,Robert Modzelewska-Banachiewicz,Bożena |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Kosmalski,Tomasz Studzińska,Renata Redka,Małgorzata Pluskota,Robert Modzelewska-Banachiewicz,Bożena |
dc.subject.por.fl_str_mv |
lipophilicity oxime ethers high-performance liquid chromatography biological activity |
topic |
lipophilicity oxime ethers high-performance liquid chromatography biological activity |
description |
Heterocyclic oxime ethers play a significant role in organisms due to their biological activity. Lipophilicity is an important parameter that may affect biological activity of the compounds 1-(benzofuran-2-yl)ethan-1-one oxime and its nine biologically active ethers. The relationship between the structure and lipophilicity parameters (log kw values) of the ten compounds is here described. Reversed phase high performance liquid chromatography (RP-HPLC) method was used having methanol, 2-propanol and acetonitrile as organic modifiers of the mobile phases. Both experimental (log kw) and calculated (log P) parameters showed to be strongly positively correlated. The weakest correlation with all the data was for the log kw methanol. For all of analyzed compounds, log kw values are smaller than 5 (except for analyses carried out in methanol), and this result corresponds to the Lipinski’s rule in the range of lipophilicity. Therefore, in the case of their use as drugs, they will be probably active after oral application. |
publishDate |
2017 |
dc.date.none.fl_str_mv |
2017-11-01 |
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=S0103-50532017001102100 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001102100 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20170055 |
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.28 n.11 2017 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_ |
1750318180013703168 |