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

Abstract

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.

Graphical abstract