Síntese de aminoálcoois derivados do D-manitol

Oliveira, Pedro Santos Mello de; Ferreira, Vı́tor F.; Souza, Marcus V. N. de; Carvalho, Erika Martins de

doi:10.1590/s0100-40422008000400013

Cited by 9 publications

(6 citation statements)

References 9 publications

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“…Considering the fundamental presence of carbohydrate, such as peptidoglycan and arabinogalactan, in the construction of the mycobacterial cell walls [17][18][19] and the reaction between INH and aldehydes (e.g. glucose and lactose) in drug formulations, 20 in this work we …”

Section: Introductionmentioning

confidence: 99%

Synthesis and antitubercular activity of isoniazid condensed with carbohydrate derivatives

et al. 2009

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Recebido em 23/9/08; aceito em 21/1/09; publicado na web em 14/7/09 A series of 13 compounds analogous of isoniazid condensed with carbohydrate was synthesized and evaluated for their in vitro antibacterial activity against Mycobacterium tuberculosis H 37 Rv using Alamar Blue susceptibility test and the activity expressed as the minimum inhibitory concentration (MIC 90 ) in µg/mL. Several compounds exhibited antitubercular activity (0.31-3.12 µg/mL) when compared with first line drugs such as isoniazid (INH) and rifampicin (RIP) and could be a good starting point to develop new compounds against tuberculosis.

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Section: Introductionmentioning

confidence: 99%

Synthesis and antitubercular activity of isoniazid condensed with carbohydrate derivatives

et al. 2009

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“…For background to the use of amino alcohols in medicinal chemistry, see: Ferreira et al (2009); de Oliveira et al (2008); Brik & Wong (2003); Ghosh et al (2001); Parikh et al (2005); Andrews et al (2006). For the anti-malarial activity of hydroxyethylpiperazines, see: .…”

Section: Related Literaturementioning

confidence: 99%

“…Amino alcohols play versatile roles in medicinal chemistry (Ferreira et al, 2009;de Oliveira et al, 2008;Brik & Wong, 2003, Ghosh et al, 2001Parikh et al, 2005;Andrews et al, 2006). Some of us recently reported the anti-malarial activity of hydroxyethypiperazines against Plasmodium falciparum and of hydroxyethylsulfonamide derivatives against Plasmodium falciparum (Cunico et al, 2008;Cunico, Gomes, Facchinetti et al, 2009), and mycobacterium tuberculosis H37Rv (Cunico et al, 2011).…”

Section: S1 Commentmentioning

confidence: 99%

N-{(2S)-3-Hydroxy-4-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-1-phenyl-2-butyl}-4-methylbenzenesulfonamide

et al. 2011

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The thiadiazoyl and sulfonyl-benzene rings in the title compound, C20H23N3O3S3, are aligned to the same side of the molecule, forming a twisted ‘U’ shape [dihedral angle = 77.6 (5)°]. The benzyl-benzene ring is orientated in the opposite direction from the molecule but projects approximately along the same axis as the other rings [dihedral angle between benzene rings = 28.2 (5)°] so that, overall, the molecule has a flattened shape. The hydroxy and amine groups are almost syn which enables the formation of intermolecular hydroxy-OH⋯N(thiadiazoyl) and amine-H⋯O(sulfonyl) hydrogen bonds leading to a supramolecular chain aligned along the a axis.

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“…!-Aminoalcohol derivatives thus appear a promising class of compounds to investigate as anti-*Address correspondence to this author at the Centro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Av. Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil; Tel: +55-2139772404; E-mail: j.wardell@abdn.ac.uk TB-HIV agents and consequently we have studied the antitubercular activities of a number of 2-hydroxyethylamine derivatives [12][13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Syntheses and Antimycobacterial Activities of [(2S,3R)-2-(Amino)-4- (Arenesulfonamido)-3-Hydroxy-1-Phenylbutane Derivatives

Moreth¹,

Gomes²,

Lourenço³

et al. 2014

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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.

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Síntese de aminoálcoois derivados do D-manitol

Cited by 9 publications

References 9 publications

Synthesis and antitubercular activity of isoniazid condensed with carbohydrate derivatives

Synthesis and antitubercular activity of isoniazid condensed with carbohydrate derivatives

N-{(2S)-3-Hydroxy-4-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-1-phenyl-2-butyl}-4-methylbenzenesulfonamide

Syntheses and Antimycobacterial Activities of [(2S,3R)-2-(Amino)-4- (Arenesulfonamido)-3-Hydroxy-1-Phenylbutane Derivatives

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