Title :

Ferrocene-based nitroheterocyclic sulfonylhydrazones: design, synthesis, characterization and trypanocidal properties.

Author(s) :

Gallardo, Miguel [Auteur]
Universidad de Concepción = University of Concepción [Chile] [UdeC]
Arancibia, Rodrigo [Auteur]
Universidad de Concepción = University of Concepción [Chile] [UdeC]
Jiménez, Claudio [Auteur]
Universidad de Concepción = University of Concepción [Chile] [UdeC]
Wilkinson, Shane [Auteur]
Queen Mary University of London [QMUL]
Toro, Patricia M [Auteur]
Universidad Autonoma de Chile
Roussel, Pascal [Auteur]
Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181
Henry, Natacha [Auteur]
Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181

Journal title :

Journal of Biological Inorganic Chemistry

Abbreviated title :

J Biol Inorg Chem

Publication date :

2023-07-19

ISSN :

1432-1327

English keyword(s) :

Type I nitroreductase
Trypanocidal agents
Nitroheterocyclic
Ferrocene
Bioorganometallics

HAL domain(s) :

Chimie/Chimie inorganique

English abstract : [en]

A series of new ferrocenyl nitroheterocyclic sulfonylhydrazones (1a-4a and 1b-2b) were prepared by the reaction between formyl (R = H) or acetyl (R = CH3) nitroheterocyclic precursors [4/5-NO2(C5H2XCOR), where X = O, S)] ...
Show more >A series of new ferrocenyl nitroheterocyclic sulfonylhydrazones (1a-4a and 1b-2b) were prepared by the reaction between formyl (R = H) or acetyl (R = CH3) nitroheterocyclic precursors [4/5-NO2(C5H2XCOR), where X = O, S)] and ferrocenyl tosyl hydrazine [(η5-C5H5)Fe(η5-C5H4SO2-NH-NH2)]. All compounds were characterized by conventional spectroscopic techniques. In the solid state, the molecular structures of compounds 1a, 2b, and 3a were determined by single-crystal X-ray diffraction. The compounds showed an E-configuration around the C=N moiety. Evaluation of trypanocidal activity, measured in vitro against the Trypanosoma cruzi and Trypanosoma brucei strains, indicated that all organometallic tosyl hydrazones displayed activity against both parasite species with a higher level of potency toward T. brucei than T. cruzi. Moreover, the biological evaluation showed that the 5-nitroheterocyclic derivatives were more efficient trypanocidal agents than their 4-nitroheterocyclic counterparts.Show less >

Language :

Anglais

Audience :

Internationale

Popular science :

Non

Administrative institution(s) :

Université de Lille
CNRS
Centrale Lille
ENSCL
Univ. Artois

Collections :

• Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181

Research team(s) :

Matériaux inorganiques, structures, systèmes et propriétés (MISSP)

Submission date :

2023-10-20T06:55:01Z
2023-11-02T16:13:48Z