Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action
Autor(a) principal: | |
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Data de Publicação: | 2021 |
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=S0103-50532021000300626 |
Resumo: | Benzodiazepines derivatives are nitrogen heterocyclic compounds that have various industrial, synthetic, and medicinal applications. Therefore, its potential fully justifies every effort towards the improvement of new, selective, and competent production of these heterocyclic compounds. The novelty of this study encompasses the synthesis of new hydroxylated analogs of 1,5-benzodiazepine together with the evaluation of their biological potential as antioxidants and antifungals candidates. Additionally, the reported antifungal activity against fungi of the Sporothrix schenckii complex inaugurates an unprecedented property for this class of compounds. The results of biological activities assays suggest that the novel 2,7-dimethyl-2,4-bis(4-hydroxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepine possesses a high antifungal activity against all fungal strains evaluated of the Sporothrix genus and outstanding total antioxidant capacity. Besides, in silico studies have evidenced that the hydroxylated derivatives have the best aqueous solubility and cell permeability profile, which makes them superior in comparison with the commercial antifungal itraconazole, a drug commonly used in the treatment of sporotrichosis. |
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Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Actionbiological activitiessolvent effectADME propertiesSporothrixBenzodiazepines derivatives are nitrogen heterocyclic compounds that have various industrial, synthetic, and medicinal applications. Therefore, its potential fully justifies every effort towards the improvement of new, selective, and competent production of these heterocyclic compounds. The novelty of this study encompasses the synthesis of new hydroxylated analogs of 1,5-benzodiazepine together with the evaluation of their biological potential as antioxidants and antifungals candidates. Additionally, the reported antifungal activity against fungi of the Sporothrix schenckii complex inaugurates an unprecedented property for this class of compounds. The results of biological activities assays suggest that the novel 2,7-dimethyl-2,4-bis(4-hydroxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepine possesses a high antifungal activity against all fungal strains evaluated of the Sporothrix genus and outstanding total antioxidant capacity. Besides, in silico studies have evidenced that the hydroxylated derivatives have the best aqueous solubility and cell permeability profile, which makes them superior in comparison with the commercial antifungal itraconazole, a drug commonly used in the treatment of sporotrichosis.Sociedade Brasileira de Química2021-03-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000300626Journal of the Brazilian Chemical Society v.32 n.3 2021reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20200217info:eu-repo/semantics/openAccessCaiana,Elizeu C.Veras,Bruno O. deSouza,Antônia L. deQueiroz,Neideeng2021-02-25T00:00:00Zoai:scielo:S0103-50532021000300626Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2021-02-25T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action |
title |
Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action |
spellingShingle |
Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action Caiana,Elizeu C. biological activities solvent effect ADME properties Sporothrix |
title_short |
Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action |
title_full |
Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action |
title_fullStr |
Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action |
title_full_unstemmed |
Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action |
title_sort |
Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action |
author |
Caiana,Elizeu C. |
author_facet |
Caiana,Elizeu C. Veras,Bruno O. de Souza,Antônia L. de Queiroz,Neide |
author_role |
author |
author2 |
Veras,Bruno O. de Souza,Antônia L. de Queiroz,Neide |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Caiana,Elizeu C. Veras,Bruno O. de Souza,Antônia L. de Queiroz,Neide |
dc.subject.por.fl_str_mv |
biological activities solvent effect ADME properties Sporothrix |
topic |
biological activities solvent effect ADME properties Sporothrix |
description |
Benzodiazepines derivatives are nitrogen heterocyclic compounds that have various industrial, synthetic, and medicinal applications. Therefore, its potential fully justifies every effort towards the improvement of new, selective, and competent production of these heterocyclic compounds. The novelty of this study encompasses the synthesis of new hydroxylated analogs of 1,5-benzodiazepine together with the evaluation of their biological potential as antioxidants and antifungals candidates. Additionally, the reported antifungal activity against fungi of the Sporothrix schenckii complex inaugurates an unprecedented property for this class of compounds. The results of biological activities assays suggest that the novel 2,7-dimethyl-2,4-bis(4-hydroxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepine possesses a high antifungal activity against all fungal strains evaluated of the Sporothrix genus and outstanding total antioxidant capacity. Besides, in silico studies have evidenced that the hydroxylated derivatives have the best aqueous solubility and cell permeability profile, which makes them superior in comparison with the commercial antifungal itraconazole, a drug commonly used in the treatment of sporotrichosis. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021-03-01 |
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=S0103-50532021000300626 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000300626 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20200217 |
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.32 n.3 2021 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_ |
1750318183963688960 |