Author | Moreth, Marcele | |
Author | Gomes, Claudia R. B. | |
Author | Lourenço, Maria C. S. | |
Author | Soares, Rodrigo P. | |
Author | Rocha, Marcele N. | |
Author | Kaiser, Carlos R. | |
Author | Souza, Marcus V. N. de | |
Author | Wardell, Solange M. S. V. N. | |
Author | Wardell, James L. | |
Access date | 2019-09-09T14:45:46Z | |
Available date | 2019-09-09T14:45:46Z | |
Document date | 2013 | |
Citation | 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. | pt_BR |
ISSN | 1573-4064 | pt_BR |
URI | https://www.arca.fiocruz.br/handle/icict/35406 | |
Language | eng | pt_BR |
Publisher | Bentham Science Publishers | pt_BR |
Rights | open access | pt_BR |
Title | Syntheses and antimycobacterial activities of [(2S,3R)-2-(amino)-4-(arenesulfonamido)-3-hydroxy-1-phenylbutane derivatives | pt_BR |
Type | Article | pt_BR |
DOI | 10.2174/15734064113099990003 | |
Abstract | 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. | pt_BR |
Affilliation | 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. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto de Pesquisas Clínicas Evandro Chagas. Departamento de Bacteriologia. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisas René Rachou. Belo Horizonte, MG, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Centro de Pesquisas René Rachou. Belo Horizonte, MG, Brasil. | pt_BR |
Affilliation | Universidade Federal do Rio de Janeiro. Instituto de Química. Rio de Janeiro, RJ, Brasil. | pt_BR |
Affilliation | 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. | pt_BR |
Affilliation | CHEMSOL. Aberdeen, Scotland. | pt_BR |
Affilliation | 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. | pt_BR |
Subject | Antimycobacterial activity | pt_BR |
Subject | Cytotoxicity | pt_BR |
Subject | Hydroxyethylamine derivatives | pt_BR |
Subject | Sulfonamide derivatives | pt_BR |
Subject | X-ray crystallography | pt_BR |
e-ISSN | 1875-6638 | |
Embargo date | 2020-09-09 | |