Show simple item record Silva, Pedro Eduardo Almeida da Soares, Daniela Fernandes Ramos Bonacorso, Helio Gauze Iglesia, Agustina de la Oliveira, Marli Redin Coelho, Tatiane Silveira Navarini, Jussara Morbidoni, Hector Zanatta, Nilo Martins, Marcos Antonio Pinto 2013-01-17T20:14:06Z 2013-01-17T20:14:06Z 2008
dc.identifier.citation SILVA, Pedro Eduardo Almeida da et al. Synthesis and in vitro antimycobacterial activity of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-4,5-dihydro-1H-1-(isonicotinoyl) pyrazoles. International Journal of Antimicrobial Agents, v. 32, p. 139-144, 2008. Disponível em: <>. Acesso em: 18 set. 2012. pt_BR
dc.identifier.issn 0924-8579
dc.description.abstract A series of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-1H-1-isonicotinoyl-4,5-dihydropyrazoles (2a–i) were synthesised by the cyclocondensation reaction of 4-methoxy-1,1,1-trifluoro[chloro]-4 (substituted)-alk-3-en-2-ones (1a–i) and isoniazid (INH). Their in vitro antimicrobial activity was tested against INH-susceptible Mycobacterium tuberculosis H37Rv, INH-resistant clinical M. tuberculosis isolates and non-tuberculous mycobacteria. Amongst the synthesised compounds, 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1 (isonicotinoyl)- pyrazole (2a) and 5-hydroxy-3-(4-methylphenyl)-5-trifluoromethyl-4,5-dihydro-1H-1-(isonicotinoyl) pyrazole (2d) were found to be the two most active agents against susceptible M. tuberculosis and several INH-resistant strains. The compound 3-(2-furyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-(isonicotinoyl)pyrazole (2f) was active against all the INH-resistant strains regardless of the genetic background at concentrations two- to four-fold its minimum inhibitory concentration against M. tuberculosis H37Rv. These compounds were inhibitors of mycolic acid biosynthesis, in agreement with the utilisation of the INH scaffold for their design. Interestingly, the most active compound against M. tuberculosis, 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-(isonicotinoyl)-pyrazole (2a),was even more potent than INH against non-tuberculous mycobacteria. pt_BR
dc.language.iso eng pt_BR
dc.rights restrict access pt_BR
dc.subject Pyrazoles pt_BR
dc.subject Pyrazolines pt_BR
dc.subject Mycobacterium tuberculosis pt_BR
dc.subject Antimycobacterial activity pt_BR
dc.title Synthesis and in vitro antimycobacterial activity of 3-substituted 5-hydroxy-5-trifluoro[chloro]methyl-4,5-dihydro-1H-1-(isonicotinoyl) pyrazoles pt_BR
dc.type article pt_BR
dc.identifier.doi 10.1016/j.ijantimicag.2008.03.019 pt_BR

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