Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives

Detalhes bibliográficos
Autor(a) principal: Moreth, Marcele
Data de Publicação: 2013
Outros Autores: Gomes, Claudia R. B., Lourenço, Maria C. S., Soares, Rodrigo P., Rocha, Marcele N., Kaiser, Carlos R., Souza, Marcus V. N. de, Wardell, Solange M. S. V. N., Wardell, James L.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/35406
Resumo: 2020-09-09
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spelling Moreth, MarceleGomes, Claudia R. B.Lourenço, Maria C. S.Soares, Rodrigo P.Rocha, Marcele N.Kaiser, Carlos R.Souza, Marcus V. N. deWardell, Solange M. S. V. N.Wardell, James L.2019-09-09T14:45:46Z2019-09-09T14:45:46Z2013MORETH, Marcele et al. Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4- (arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives. Medicinal Chemistry, v. 9, p. 1-12, 2013.1573-4064https://www.arca.fiocruz.br/handle/icict/3540610.2174/157340641130999900031875-6638engBentham Science PublishersSyntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivativesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article2020-09-09Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Pesquisas Clínicas Evandro Chagas. Departamento de Bacteriologia. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Centro de Pesquisas René Rachou. Belo Horizonte, MG, Brasil.Fundação Oswaldo Cruz. Centro de Pesquisas René Rachou. Belo Horizonte, MG, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Rio de Janeiro, RJ, Brasil.CHEMSOL. Aberdeen, Scotland.Fundação Oswaldo Cruz. Centro de Desenvolvimento Tecnológico em Saúde. Rio de Janeiro, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Rio de Janeiro, RJ, Brasil.The syntheses of hydroxyethylsulfonamides, (2S,3R)-tert-butyl N-[4-(N-benzyl-4-R-phenylsulfonamido)-3- hydroxy-1-phenylbutan-2-yl]carbamates and (5) (2S,3R)-2-amino-4-[N-benzyl-4-R-benzenesulfonamido]-3-hydroxy-1-phenylbutane hydrochlorides (6), derived from (2S,3S)-Boc-phenylalanine epoxide, are reported. None of the compounds, containing the Boc group, showed activity against M. tuberculosis ATTC 27294, while compounds 6 did, with the most active compounds having R = p-Cl, p-Br and p-Me. Results indicate that the presence of a free amino group at C2 and the sulphonamide moiety are important for biological activity. The antimycobacterial activity of compounds 6 correlated well with the calculated lipophilicities, but not with the electronic effects of the substituents, R. All compounds 6 were highly cytotoxic against the hepatoma cell lineage Hep G2 A16. The X-ray crystal structure of compound [(6: R = Me).H2O] is also reported. In the propeller-like conformation adopted by the cation, the amino and hydroxy groups have a cis arrangement, and thus are suitably placed to form 5- membered chelates.Antimycobacterial activityCytotoxicityHydroxyethylamine derivativesSulfonamide derivativesX-ray crystallographyinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txttext/plain1748https://www.arca.fiocruz.br/bitstream/icict/35406/1/license.txt8a4605be74aa9ea9d79846c1fba20a33MD51ORIGINALve_Moreth_Marcele_etal_INI_2013.pdfve_Moreth_Marcele_etal_INI_2013.pdfapplication/pdf1812766https://www.arca.fiocruz.br/bitstream/icict/35406/2/ve_Moreth_Marcele_etal_INI_2013.pdf72f03b80a5859753fa6e88c8d8a9fa08MD52TEXTve_Moreth_Marcele_etal_INI_2013.pdf.txtve_Moreth_Marcele_etal_INI_2013.pdf.txtExtracted texttext/plain51174https://www.arca.fiocruz.br/bitstream/icict/35406/3/ve_Moreth_Marcele_etal_INI_2013.pdf.txt6564c3c990bcc454c8e22a44284b7106MD53icict/354062021-03-24 16:32:36.238oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352021-03-24T19:32:36Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false
dc.title.pt_BR.fl_str_mv Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives
title Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives
spellingShingle Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives
Moreth, Marcele
Antimycobacterial activity
Cytotoxicity
Hydroxyethylamine derivatives
Sulfonamide derivatives
X-ray crystallography
title_short Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives
title_full Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives
title_fullStr Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives
title_full_unstemmed Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives
title_sort Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives
author Moreth, Marcele
author_facet Moreth, Marcele
Gomes, Claudia R. B.
Lourenço, Maria C. S.
Soares, Rodrigo P.
Rocha, Marcele N.
Kaiser, Carlos R.
Souza, Marcus V. N. de
Wardell, Solange M. S. V. N.
Wardell, James L.
author_role author
author2 Gomes, Claudia R. B.
Lourenço, Maria C. S.
Soares, Rodrigo P.
Rocha, Marcele N.
Kaiser, Carlos R.
Souza, Marcus V. N. de
Wardell, Solange M. S. V. N.
Wardell, James L.
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Moreth, Marcele
Gomes, Claudia R. B.
Lourenço, Maria C. S.
Soares, Rodrigo P.
Rocha, Marcele N.
Kaiser, Carlos R.
Souza, Marcus V. N. de
Wardell, Solange M. S. V. N.
Wardell, James L.
dc.subject.en.pt_BR.fl_str_mv Antimycobacterial activity
Cytotoxicity
Hydroxyethylamine derivatives
Sulfonamide derivatives
X-ray crystallography
topic Antimycobacterial activity
Cytotoxicity
Hydroxyethylamine derivatives
Sulfonamide derivatives
X-ray crystallography
description 2020-09-09
publishDate 2013
dc.date.issued.fl_str_mv 2013
dc.date.accessioned.fl_str_mv 2019-09-09T14:45:46Z
dc.date.available.fl_str_mv 2019-09-09T14:45:46Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.citation.fl_str_mv MORETH, Marcele et al. Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4- (arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives. Medicinal Chemistry, v. 9, p. 1-12, 2013.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/35406
dc.identifier.issn.pt_BR.fl_str_mv 1573-4064
dc.identifier.doi.none.fl_str_mv 10.2174/15734064113099990003
dc.identifier.eissn.none.fl_str_mv 1875-6638
identifier_str_mv MORETH, Marcele et al. Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4- (arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives. Medicinal Chemistry, v. 9, p. 1-12, 2013.
1573-4064
10.2174/15734064113099990003
1875-6638
url https://www.arca.fiocruz.br/handle/icict/35406
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Bentham Science Publishers
publisher.none.fl_str_mv Bentham Science Publishers
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
instname:Fundação Oswaldo Cruz (FIOCRUZ)
instacron:FIOCRUZ
instname_str Fundação Oswaldo Cruz (FIOCRUZ)
instacron_str FIOCRUZ
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reponame_str Repositório Institucional da FIOCRUZ (ARCA)
collection Repositório Institucional da FIOCRUZ (ARCA)
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