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Title

Ferrocenyl and cyrhetrenyl azines containing a 5-nitroheterocyclic moiety: synthesis, structural characterization, electrochemistry and evaluation as anti-Trypanosoma cruzi agents

AuthorsGómez, Johana; Klahn, A. Hugo; Fuentealba, Mauricio; Sierra, Diego; Olea-Azar, Claudio; Maya, Juan D.; Medina, Manuela E. CSIC
KeywordsChagas disease
Cyclic voltammetry
Trypanosoma cruzi
Structural characterization
Ferrocenyl azines
Cyrhetrenyl azines
Issue Date15-Jun-2017
PublisherElsevier
CitationJournal of Organometallic Chemistry 839: 108-115 (2017)
AbstractThe synthesis of unsymmetrical ferrocenyl and cyrhetrenyl azines [(η-CH)-CR=N-N=CH-2-CHX-5-NO]M (M=Re(CO), Fe(η-CH); R = H, CH, X = O, S) has led to the development of new derivatives of 5-nitroheterocycles as potential anti-trypanosomal agents. The structures of compounds have been confirmed using conventional spectroscopic techniques (FT-IR, H and C NMR), mass spectrometry, including single-crystal X-ray diffraction analysis of compounds 2NT and 4NT. Based on the chemical shifts of the iminic carbons (C, C) and the reduction potential of the nitro group (E), an extensive π-conjugation of the azine bridge (-C(R)=N-N=CH-) was observed along with a correlation between the opposing electronic effects of the cyrhetrenyl and ferrocenyl fragments. It was established that the existence of an electron-withdrawing group (cyrhetrene) could facilitate the generation of radical species (RNO to RNO ) through the azine bridge. The organometallic azines were evaluated for anti-trypanosomal activity in vitro against the epimastigote form of the Dm28c strain of T. cruzi, yielding IC values in the low micromolar range.
Publisher version (URL)https://doi.org/10.1016/j.jorganchem.2017.03.014
URIhttp://hdl.handle.net/10261/188662
DOI10.1016/j.jorganchem.2017.03.014
Identifiersdoi: 10.1016/j.jorganchem.2017.03.014
issn: 0022-328X
Appears in Collections:(ICMM) Artículos

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