Cyrhetrenyl and cymantrenyl N-acylhydrazone complexes based on isoniazid: Synthesis, characterization, X-ray crystal structures and antitubercular activity evaluation

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Autor(es): dc.contributorPontificia Universidad Católica de Valparaíso-
Autor(es): dc.contributorUniversidade Estadual Paulista (UNESP)-
Autor(es): dc.contributorUniversidad de Santiago de Chile-
Autor(es): dc.contributorUniversidad Adolfo Ibáñez-
Autor(es): dc.creatorMallea, Mario-
Autor(es): dc.creatorAcuña, Alejandra-
Autor(es): dc.creatorKlahn, A. Hugo-
Autor(es): dc.creatorArtigas, Vania-
Autor(es): dc.creatorPavan, Fernando Rogério-
Autor(es): dc.creatorDemarqui, Fernanda Manaia-
Autor(es): dc.creatorLemus, Luis-
Autor(es): dc.creatorJara, Danilo H.-
Autor(es): dc.creatorToro, Patricia M.-
Data de aceite: dc.date.accessioned2025-08-21T17:04:41Z-
Data de disponibilização: dc.date.available2025-08-21T17:04:41Z-
Data de envio: dc.date.issued2022-05-01-
Data de envio: dc.date.issued2022-05-01-
Data de envio: dc.date.issued2022-04-15-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1016/j.jorganchem.2022.122299-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/234257-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/234257-
Descrição: dc.descriptionFour organometallic N-acylhydrazones of the general formulae [M{(η5-C5H4)-CH[dbnd]N[sbnd]NH[sbnd]C(O)-(C5H4[sbnd]N)}(CO)3] [(with M = Re (5a) or Mn (6a)] and [M{(η5-C5H4)-C(Me)=N[sbnd]NH[sbnd]C(O)-(C5H4[sbnd]N)}(CO)3] [(with M = Re (5b) or Mn (6b)] were prepared by reaction of aldehyde/methyl ketone organometallic precursors with isoniazid (INH). All compounds were fully characterized using conventional spectroscopic techniques (FT-IR, 1H and 13C{1H} NMR, mass spectrometry, and high-resolution mass spectrometry). The X-ray crystal structures of cyrhetrenyl compounds (5a and 5b) are also reported. This structural analysis indicated that both compounds exhibited an E-configuration of the substituents on the -C(R1)=N- (R1 = H or Me). The biological activity of the four analogous organometallic compounds (5 and 6) to INH and their organics counterpart {[(C6H5)-C(R)=N[sbnd]NH[sbnd]C(O)-(C5H4[sbnd]N)] where R = H (NAH[sbnd]H) or R = Me (NAH-Me)} were evaluated on Mycobacterium tuberculosis (M. tuberculosis) in the standard strain H37Rv ATCC 27,294. The replacement of a hydrogen atom by a methyl group on the acylhydrazone moiety led to a significant increase in antitubercular properties. The compounds 5b and 6b (R1 = Me) were at least 36- and 18-fold more effective than 5a and 6a (R1 = H), respectively. The cyrhetrenyl derivative (5b) was the most active complex against M. tuberculosis. This compound was shown to be about 2-times more effective than its organic analog (NAH-Me) and showed activity comparable to antitubercular drug INH. In vitro toxicity assays against murine macrophage cells J774A.1 (ATCC TIB-67) were also conducted, and selectivity indexes were determined for the most promising compounds. All N-acylhydrazones showed a moderated cytotoxic profile, similar to the isoniazid and rifampicin (RIF) control drugs, while 5b exhibited better selectivity index (SI) concerning the organic counterpart NAH-Me. Based on the anti-TB activity, cytotoxicity, and selectivity index, compound 5b has more potential for evolution as a new antitubercular agent.-
Descrição: dc.descriptionInstituto de Química Pontificia Universidad Católica de Valparaíso, Valparaíso-
Descrição: dc.descriptionSao Paulo State University (UNESP) School of Pharmaceutical Sciences, SP-
Descrição: dc.descriptionFacultad de Química y Biología Universidad de Santiago de Chile, Alameda 3363, Estación Central-
Descrição: dc.descriptionFacultad de Ingeniería y Ciencias Universidad Adolfo Ibáñez, Av. Padre Hurtado 750-
Descrição: dc.descriptionSao Paulo State University (UNESP) School of Pharmaceutical Sciences, SP-
Idioma: dc.languageen-
Relação: dc.relationJournal of Organometallic Chemistry-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectCrystal structures-
Palavras-chave: dc.subjectCymantrenyl-
Palavras-chave: dc.subjectCyrhetrenyl-
Palavras-chave: dc.subjectIsoniazid-
Palavras-chave: dc.subjectMycobacterium tuberculosis-
Título: dc.titleCyrhetrenyl and cymantrenyl N-acylhydrazone complexes based on isoniazid: Synthesis, characterization, X-ray crystal structures and antitubercular activity evaluation-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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