Organometallic <i>N</i>-acylhydrazones of 5-nitrofuran and 5-nitrothiophene based: Synthesis, electrochemical, antiparasitic evaluation, and computational study

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dc.contributor.authorSaldias, Marianela
dc.contributor.authorAcuna, Alejandra
dc.contributor.authorMellado, Marco
dc.contributor.authorWilkinson, Shane R.
dc.contributor.authorMoncada-Basualto, Mauricio
dc.contributor.authorArtigas, Vania
dc.contributor.authorFuentealba, Mauricio
dc.contributor.authorLucero, Andrea
dc.contributor.authorOyarzo, Juan
dc.contributor.authorToro, Patricia M.
dc.date.accessioned2025-01-20T17:33:54Z
dc.date.available2025-01-20T17:33:54Z
dc.date.issued2023
dc.description.abstractIn searching for new therapeutic agents for treating American trypanosomiasis and Human African trypanosomiasis, four nitroheterocyclic acylhydrazones of general formulae [R1-CH=N-NH-C(O)-(5-C4H2X)] (where R1 = ferrocenyl or cyrhetrenyl, and X = O or S) have been synthesized and characterized by spectroscopic techniques. Comparative studies of their stability by 1H-NMR and UV-Vis experiments were reported. Single-crystal X-ray diffraction confirmed the molecular structures of NF-1 and NT-2. Their X-ray crystal structures reveal that both adopt an E-configuration on the C=N moiety. Regarding the -NH-C(O)- bond, the structure of NF-1 confirmed a trans conformation, while NT-2 exhibited a cis-amide conformation. The cyclic voltammetry and electron spin resonance (ESR) experiments were conducted to study the electrochemical behavior of N-acylhydrazones. The antiparasitic activities of compounds against Trypanosoma cruzi (epimastigotes) and Trypanosoma brucei (trypomastigotes) revealed that cyrhetrenyl complexes were more effective than their ferrocenyl analogs. The cyrhetrenyl derivative NT-2 (EC50 = 2.25 mu M) showed activity against T. brucei comparable to the standard drug nifurtimox (Nfx, EC50 = 3.56 mu M). The ferrocenyl compound NT-1 (>200 mu M) was at least two times less cytotoxic than the Nfx (88.7 mu M) against the L-6 rat skeletal myoblast cell line and exhibited a selectivity like Nfx toward T. brucei. Density functional theory (DFT) calculations were utilized as an approximation to explain the impact of organometallic and heterocyclic rings on antiparasitic activities. This study supported the experimental results, confirming that the cyrhetrenyl fragment in N-acylhydrazone derivatives plays a significant role in the antitrypanosomal activity, which can be attributed to an increase in positive charge on the metal.
dc.fuente.origenWOS
dc.identifier.doi10.1002/aoc.7263
dc.identifier.eissn1099-0739
dc.identifier.issn0268-2605
dc.identifier.urihttps://doi.org/10.1002/aoc.7263
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/91650
dc.identifier.wosidWOS:001077467100001
dc.issue.numero12
dc.language.isoen
dc.revistaApplied organometallic chemistry
dc.rightsacceso restringido
dc.subjectantiparasitic activity
dc.subjectcrystal structures
dc.subjectelectrochemical
dc.subjectorganometallic N-acylhydrazones
dc.subjectstructure-activity relationship (SAR)
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleOrganometallic <i>N</i>-acylhydrazones of 5-nitrofuran and 5-nitrothiophene based: Synthesis, electrochemical, antiparasitic evaluation, and computational study
dc.typeartículo
dc.volumen37
sipa.indexWOS
sipa.trazabilidadWOS;2025-01-12
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