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

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-carbald...

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Autores principales:	Fernando Carrasco, Wilfredo Hernández, Oscar Chupayo, Patricia Sheen, Mirko Zimic, Jorge Coronel, Celedonio M. Álvarez, Sergio Ferrero, Sandra Oramas-Royo, Evgenia Spodine, Jesus M. Rodilla, Juan Z. Dávalos
Formato:	article
Lenguaje:	EN
Publicado:	Hindawi Limited 2021
Materias:	Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/bbc875c3dcf94f21b784471c292f9569
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spelling	oai:doaj.org-article:bbc875c3dcf94f21b784471c292f95692021-11-08T02:36:02ZPhenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity2090-907110.1155/2021/6014093https://doaj.org/article/bbc875c3dcf94f21b784471c292f95692021-01-01T00:00:00Zhttp://dx.doi.org/10.1155/2021/6014093https://doaj.org/toc/2090-9071Eight 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.Fernando CarrascoWilfredo HernándezOscar ChupayoPatricia SheenMirko ZimicJorge CoronelCeledonio M. ÁlvarezSergio FerreroSandra Oramas-RoyoEvgenia SpodineJesus M. RodillaJuan Z. DávalosHindawi LimitedarticleChemistryQD1-999ENJournal of Chemistry, Vol 2021 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Chemistry QD1-999
spellingShingle	Chemistry QD1-999 Fernando Carrasco Wilfredo Hernández Oscar Chupayo Patricia Sheen Mirko Zimic Jorge Coronel Celedonio M. Álvarez Sergio Ferrero Sandra Oramas-Royo Evgenia Spodine Jesus M. Rodilla Juan Z. Dávalos Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity
description	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.
format	article
author	Fernando Carrasco Wilfredo Hernández Oscar Chupayo Patricia Sheen Mirko Zimic Jorge Coronel Celedonio M. Álvarez Sergio Ferrero Sandra Oramas-Royo Evgenia Spodine Jesus M. Rodilla Juan Z. Dávalos
author_facet	Fernando Carrasco Wilfredo Hernández Oscar Chupayo Patricia Sheen Mirko Zimic Jorge Coronel Celedonio M. Álvarez Sergio Ferrero Sandra Oramas-Royo Evgenia Spodine Jesus M. Rodilla Juan Z. Dávalos
author_sort	Fernando Carrasco
title	Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity
title_short	Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity
title_full	Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity
title_fullStr	Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity
title_full_unstemmed	Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity
title_sort	phenylisoxazole-3/5-carbaldehyde isonicotinylhydrazone derivatives: synthesis, characterization, and antitubercular activity
publisher	Hindawi Limited
publishDate	2021
url	https://doaj.org/article/bbc875c3dcf94f21b784471c292f9569
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Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity

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