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

14 pags, 5 figs, 3 tabs, 1 sch

Detalles Bibliográficos
Autores: Carrasco, Fernando, Hernández, Wilfredo, Chupayo, Oscar, Sheen, Patricia, Zimic, Mirko, Coronel, Jorge, Álvarez, Celedonio M., Ferrero, Sergio, Oramas-Royo, Sandra, Spodine, Evgenia, Rodilla, Jesus M., Dávalos, J.Z.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/258709
Acceso en línea:http://hdl.handle.net/10261/258709
https://api.elsevier.com/content/abstract/scopus_id/85118949427
Access Level:acceso abierto
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spelling Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular ActivityCarrasco, FernandoHernández, WilfredoChupayo, OscarSheen, PatriciaZimic, MirkoCoronel, JorgeÁlvarez, Celedonio M.Ferrero, SergioOramas-Royo, SandraSpodine, EvgeniaRodilla, Jesus M.Dávalos, J.Z.14 pags, 5 figs, 3 tabs, 1 schEight 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.W. H. and F. C. acknowledge Universidad de Lima Scientific Research Institute for the financial support to carry out this research work. E. S. thanks Financiamiento Basal para Centros Cientificos y Tecnologicos de Excelencia, AFB10008. J. Z. D. thanks Consejo Superior de Investigacion Cientifica (CSIC, Spain). S. O. thanks Ministerio de Ciencias, Innovacion y Universidades (MICINN (RTI2018-094356-B-C21)) and Cabildo de Tenerife (Agust ' in de Betancourt Program).Peer reviewedHindawi Publishing CorporationUniversidad de LimaComisión Nacional de Investigación Científica y Tecnológica (Chile)Consejo Superior de Investigaciones Científicas (España)Ministerio de Ciencia, Innovación y Universidades (España)Cabildo de TenerifeCarrasco, Fernando [0000-0002-7746-8627]Hernández, Wilfredo [0000-0002-6122-4935]Chupayo, Oscar [0000-0003-1955-7071]Sheen, Patricia [0000-0002-7118-9301]Zimic, Mirko [0000-0002-7203-8847]Coronel, Jorge [0000-0002-4580-6716]Álvarez, Celedonio M. [0000-0003-4431-6501]Ferrero, Sergio [0000-0003-2334-1169]Oramas-Royo, Sandra [0000-0001-7768-1498]Spodine, Evgenia [0000-0002-7089-3145]Rodilla, Jesus M. [0000-0001-6114-3572]Dávalos, J.Z. [0000-0002-5835-6371]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202220222021info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/258709https://api.elsevier.com/content/abstract/scopus_id/85118949427reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-094356-B-C21Journal of Chemistryhttps://doi.org/10.1155/2021/6014093Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2587092026-05-22T06:33:51Z
dc.title.none.fl_str_mv Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity
title Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity
spellingShingle Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity
Carrasco, Fernando
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
dc.creator.none.fl_str_mv Carrasco, Fernando
Hernández, Wilfredo
Chupayo, Oscar
Sheen, Patricia
Zimic, Mirko
Coronel, Jorge
Álvarez, Celedonio M.
Ferrero, Sergio
Oramas-Royo, Sandra
Spodine, Evgenia
Rodilla, Jesus M.
Dávalos, J.Z.
author Carrasco, Fernando
author_facet Carrasco, Fernando
Hernández, Wilfredo
Chupayo, Oscar
Sheen, Patricia
Zimic, Mirko
Coronel, Jorge
Álvarez, Celedonio M.
Ferrero, Sergio
Oramas-Royo, Sandra
Spodine, Evgenia
Rodilla, Jesus M.
Dávalos, J.Z.
author_role author
author2 Hernández, Wilfredo
Chupayo, Oscar
Sheen, Patricia
Zimic, Mirko
Coronel, Jorge
Álvarez, Celedonio M.
Ferrero, Sergio
Oramas-Royo, Sandra
Spodine, Evgenia
Rodilla, Jesus M.
Dávalos, J.Z.
author2_role author
author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidad de Lima
Comisión Nacional de Investigación Científica y Tecnológica (Chile)
Consejo Superior de Investigaciones Científicas (España)
Ministerio de Ciencia, Innovación y Universidades (España)
Cabildo de Tenerife
Carrasco, Fernando [0000-0002-7746-8627]
Hernández, Wilfredo [0000-0002-6122-4935]
Chupayo, Oscar [0000-0003-1955-7071]
Sheen, Patricia [0000-0002-7118-9301]
Zimic, Mirko [0000-0002-7203-8847]
Coronel, Jorge [0000-0002-4580-6716]
Álvarez, Celedonio M. [0000-0003-4431-6501]
Ferrero, Sergio [0000-0003-2334-1169]
Oramas-Royo, Sandra [0000-0001-7768-1498]
Spodine, Evgenia [0000-0002-7089-3145]
Rodilla, Jesus M. [0000-0001-6114-3572]
Dávalos, J.Z. [0000-0002-5835-6371]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description 14 pags, 5 figs, 3 tabs, 1 sch
publishDate 2021
dc.date.none.fl_str_mv 2021
2022
2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/258709
https://api.elsevier.com/content/abstract/scopus_id/85118949427
url http://hdl.handle.net/10261/258709
https://api.elsevier.com/content/abstract/scopus_id/85118949427
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-094356-B-C21
Journal of Chemistry
https://doi.org/10.1155/2021/6014093
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Hindawi Publishing Corporation
publisher.none.fl_str_mv Hindawi Publishing Corporation
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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