SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN D
Autor(a) principal: | |
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Data de Publicação: | 2015 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Química Nova (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422015001001282 |
Resumo: | A series of six new palmitic acid-based neoglycolipids related to Papulacandin D were synthesized in five steps, resulting in good yields, and they were evaluated against Candida spp. All twelve synthetic intermediates were also evaluated. The synthesis involved the initial glycosylation of two phenols (4-hydroxy-3-methoxybenzaldehyde and 3-hydroxybenzaldehyde) via their reaction with peracetylated glucosyl bromide. This was followed by deacetylation with potassium methoxide/metanol solution and the protection of two hydroxyls (C4 and C6 positions) of the saccharide unit as benzilidene acetals (10-11). The next step involved the acylation of the acetal derivatives with palmitic acid, thereby affording a mixture of two isomers mono-acylated at the C2 and C3 positions and a di-acylated product (12-17). After being isolated, each compound was subjected to the removal of the acetal protecting group to yield the papulacandin D analogues 18-23. Three compounds showed low antifungal activity against two species: C. albicans (compounds 7 and 23) and C. tropicalis (compound 17) at 200 µg mL−1. |
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SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN Dpapulacandin Dneoglycolipidspalmitic acidanaloguesantifungal activityA series of six new palmitic acid-based neoglycolipids related to Papulacandin D were synthesized in five steps, resulting in good yields, and they were evaluated against Candida spp. All twelve synthetic intermediates were also evaluated. The synthesis involved the initial glycosylation of two phenols (4-hydroxy-3-methoxybenzaldehyde and 3-hydroxybenzaldehyde) via their reaction with peracetylated glucosyl bromide. This was followed by deacetylation with potassium methoxide/metanol solution and the protection of two hydroxyls (C4 and C6 positions) of the saccharide unit as benzilidene acetals (10-11). The next step involved the acylation of the acetal derivatives with palmitic acid, thereby affording a mixture of two isomers mono-acylated at the C2 and C3 positions and a di-acylated product (12-17). After being isolated, each compound was subjected to the removal of the acetal protecting group to yield the papulacandin D analogues 18-23. Three compounds showed low antifungal activity against two species: C. albicans (compounds 7 and 23) and C. tropicalis (compound 17) at 200 µg mL−1.Sociedade Brasileira de Química2015-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422015001001282Química Nova v.38 n.10 2015reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0100-4042.20150156info:eu-repo/semantics/openAccessSouza,Thiago Belarmino deBretas,Ana Carolina OliveiraAlves,Ricardo JoséMagalhães,Thais Furtado FerreiraStoianoff,Maria Aparecida Resendeeng2015-12-17T00:00:00Zoai:scielo:S0100-40422015001001282Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2015-12-17T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN D |
title |
SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN D |
spellingShingle |
SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN D Souza,Thiago Belarmino de papulacandin D neoglycolipids palmitic acid analogues antifungal activity |
title_short |
SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN D |
title_full |
SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN D |
title_fullStr |
SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN D |
title_full_unstemmed |
SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN D |
title_sort |
SYNTHESIS AND ANTIFUNGAL ACTIVITY OF PALMITIC ACID-BASED NEOGLYCOLIPIDS RELATED TO PAPULACANDIN D |
author |
Souza,Thiago Belarmino de |
author_facet |
Souza,Thiago Belarmino de Bretas,Ana Carolina Oliveira Alves,Ricardo José Magalhães,Thais Furtado Ferreira Stoianoff,Maria Aparecida Resende |
author_role |
author |
author2 |
Bretas,Ana Carolina Oliveira Alves,Ricardo José Magalhães,Thais Furtado Ferreira Stoianoff,Maria Aparecida Resende |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Souza,Thiago Belarmino de Bretas,Ana Carolina Oliveira Alves,Ricardo José Magalhães,Thais Furtado Ferreira Stoianoff,Maria Aparecida Resende |
dc.subject.por.fl_str_mv |
papulacandin D neoglycolipids palmitic acid analogues antifungal activity |
topic |
papulacandin D neoglycolipids palmitic acid analogues antifungal activity |
description |
A series of six new palmitic acid-based neoglycolipids related to Papulacandin D were synthesized in five steps, resulting in good yields, and they were evaluated against Candida spp. All twelve synthetic intermediates were also evaluated. The synthesis involved the initial glycosylation of two phenols (4-hydroxy-3-methoxybenzaldehyde and 3-hydroxybenzaldehyde) via their reaction with peracetylated glucosyl bromide. This was followed by deacetylation with potassium methoxide/metanol solution and the protection of two hydroxyls (C4 and C6 positions) of the saccharide unit as benzilidene acetals (10-11). The next step involved the acylation of the acetal derivatives with palmitic acid, thereby affording a mixture of two isomers mono-acylated at the C2 and C3 positions and a di-acylated product (12-17). After being isolated, each compound was subjected to the removal of the acetal protecting group to yield the papulacandin D analogues 18-23. Three compounds showed low antifungal activity against two species: C. albicans (compounds 7 and 23) and C. tropicalis (compound 17) at 200 µg mL−1. |
publishDate |
2015 |
dc.date.none.fl_str_mv |
2015-12-01 |
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=S0100-40422015001001282 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422015001001282 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.5935/0100-4042.20150156 |
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 |
Química Nova v.38 n.10 2015 reponame:Química Nova (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Química Nova (Online) |
collection |
Química Nova (Online) |
repository.name.fl_str_mv |
Química Nova (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
quimicanova@sbq.org.br |
_version_ |
1750318117121163264 |