Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity: Synthesis, Characterization, and Antitubercular Activity

Título traducido de la contribución: Derivados del fenilisoxazol-3/5-carbaldehído isonicotinilhidrazona: Síntesis, caracterización, y actividad antitubercular

Fernando Carlos Carrasco Solis, Wilfredo Román Hernandez Gorritti, Oscar Chupayo, Patricia Sheen, Mirko Zimic, Jorge Coronel, Celedonio M. Álvarez, Sergio Ferrero, Sandra Oramas-Royo, Evgenia Spodine, Jesus M. Rodilla, Juan Z. Dávalos

Resultado de la investigación: Contribución a una revistaArtículo (Contribución a Revista)revisión exhaustiva


Eight new phenylisoxazole isoniazid derivatives, 3-(2′-fluorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (1), 3-
(2′-methoxyphenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (2), 3-(2′-chlorophenyl)isoxazole-5-carbaldehyde
isonicotinylhydrazone (3), 3-(3′-clorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (4), 3-(4′-bromophenyl)
isoxazole-5-carbaldehyde isonicotinylhydrazone (5), 5-(4′-methoxiphenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (6), 5-
(4′-methylphenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (7), and 5-(4′-clorophenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone
(8), have been synthesized and characterized by FT-IR, 1H-NMR, 13C-NMR, and mass spectral data. The 2D
NMR (1H-1H NOESY) analysis of 1 and 2 confirmed that these compounds in acetone-d6 are in the trans(E) isomeric form. This
evidence is supported by computational calculations which were performed for compounds 1–8, using DFT/B3LYP level with the 6-
311++G(d,p) basis set. The in vitro antituberculous activity of all the synthesized compounds was determined against the Mycobacterium
tuberculosis standard strains: sensitive H37Rv (ATCC-27294) and resistant TB DM97. All the compounds exhibited
moderate bioactivity (MIC= 0.34–0.41 μM) with respect to the isoniazid drug (MIC =0.91 μM) against the H37Rv sensitive strain.
Compounds 6 (X= 4′-OCH3) and 7 (X= 4′-CH3) with MIC values of 12.41 and 13.06 μM, respectively, were about two times more
cytotoxic, compared with isoniazid, against the resistant strain TB DM97.
Título traducido de la contribuciónDerivados del fenilisoxazol-3/5-carbaldehído isonicotinilhidrazona: Síntesis, caracterización, y actividad antitubercular
Idioma originalInglés
Número de artículoID 6014093
Número de páginas14
Publicaciónjournal of chemistry
N.ºID 6014093
Fecha en línea anticipada31 oct. 2021
EstadoPublicada - 31 oct. 2021


Profundice en los temas de investigación de 'Derivados del fenilisoxazol-3/5-carbaldehído isonicotinilhidrazona: Síntesis, caracterización, y actividad antitubercular: Synthesis, Characterization, and Antitubercular Activity'. En conjunto forman una huella única.

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